


A Teen Wolf Kinktober (2020)

by baldersgratetoo



Series: Kinktober [1]
Category: Teen Wolf (TV)
Genre: Armpit Kink, Blood, Blood Kink, Body Worship, Bodyswap, Bondage, Boot Worship, Branding, Breathplay, Breeding, Bukkake, Burnplay, CBT, Casting Couch, Cheating, Cheating Derek Hale, Choking, Clone Sex, Cock & Ball Torture, Cock Cages, Cock Warming, Comeplay, Creampie, Crossdressing, Dacryphilia, Daddy Kink, Deepthroating, Double Penetration, Dubious Consent, Emetophilia, Exhibitionism, Fat Derek Hale, Feeder Stiles Stilinski, Feeding, Feet, Fisting, Food Sex, Foot Fetish, Formalwear, Free Use, Frottage, Fucking Machines, Glory Hole, Gun Kink, Gunplay, Hate Sex, Human Furniture, Humiliation, Impact Play, Incest, Inflation, Intercrural Sex, Kinktober, Kinktober 2020, Lactation, Lactation Kink, Latex, Leather Kink, Lingerie, M/M, Male Lactation, Masochism, Massage, Master/Pet, Master/Slave, Masturbation, Medical Kink, Mirror Sex, Multi, Netorare, Non-Consensual Voyeurism, Object Insertion, Objectification, Omorashi, Orgasm Delay/Denial, Orgasm Denial, Orgy, Overstimulation, Paralysis, Pegging, Pet Play, Porn, Praise Kink, Prostate Massage, Prostitution, Public Sex, Rimming, Role Reversal, Sadism, Scat, Selfcest, Sensory Deprivation, Sex Toys, Shotgunning, Shower Sex, Sibling Incest, Size Difference, Somnophilia, Sounding, Spanking, Spitroasting, Stockings, Stripping, Sweat, Telepathic Bond, Temperature Play, Tentacle Dick, Tentacle Sex, Tentacles, Threesome - M/M/M, Tickling, Titfucking, Twincest, Under-negotiated Kink, Urethral Play, Urination, Vomiting, Voyeurism, Wall Sex, Watersports, Wax Play, Whipped Cream, Xenophilia, distention, dubcon, feederism, fuck machine, ntr, puke
Language: English
Status: Completed
Published: 2020-10-29
Updated: 2020-11-18
Packaged: 2021-03-09 05:54:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 32
Words: 50,646
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27269785
Author URL: https://archiveofourown.org/users/baldersgratetoo/pseuds/baldersgratetoo
Summary: 31 days of Teen Wolf kink prompts. See chapter 1 for a full contents of each days prompts. There's a wide section of dirty things for the pack and their friends to get up to.
Relationships: Aiden/Ethan (Teen Wolf), Chris Argent/Derek Hale, Chris Argent/Derek Hale/Jordan Parrish, Corey Bryant/Derek Hale/Stiles Stilinski, Derek Hale/David Whittemore, Derek Hale/Ethan/Jackson Whittemore, Derek Hale/Everyone, Derek Hale/Isaac Lahey, Derek Hale/Jordan Parrish/Theo Raeken, Derek Hale/Stiles Stilinski, Derek Hale/Theo Raeken, Derek Hale/Theo Raken/Original Male Character, Derek/Original Male Character(s), Ethan/Danny Mahealani/Jackson Whittemore, Ethan/Jackson Whittemore, Jordan Parrish/Sheriff Stilinski, Liam Dunbar/Derek Hale/Stiles Stilinski, Liam Dunbar/Derek Hale/Theo Raeken/Stiles Stilinski, Liam Dunbar/Stiles Stilinski, Liam Dunbar/Theo Raeken, Stiles Stilinski/Stiles Stilinski, Theo Raeken/Stiles Stilinski
Series: Kinktober [1]
Series URL: https://archiveofourown.org/series/1991107
Comments: 52
Kudos: 290





	1. Day 0 - a.k.a. introduction and contents

I was a bit late off the mark, so I’m playing catch-up. I’ve got the plot set for each day and I’m trying to use as many of each days prompts as I can. I’ve a few days completed so hopefully it shouldn’t be too far into November until I manage to finish writing, editing, a posting this Kinktober.

As of October 29th - Day 31 is a free day, and I’ve not yet decided what the theme should be. If you really want to see something let me know in the comments or on my Twitter. If it changes from ’Day 31 - ?’ In the contents below to include a kink and pairing with a link then its done and you’re too late! But if you’ve got good ideas I still want them because I’m greedy for smut prompts.

Link to the post and pictures of the prompt list are embedded below. Each day 1-30 has 3 kinks, so if there’s less than 3 listed from me then I’ve missed something out either because I couldn’t write it or couldn’t find a way to fit it in with the other 2.

> <https://t.co/FQebGUwTwo> [pic.twitter.com/mdxxqQN9jS](https://t.co/mdxxqQN9jS)
> 
> — Kinktober2020 (@kinktober2020) [August 8, 2020](https://twitter.com/kinktober2020/status/1292137619640459272?ref_src=twsrc%5Etfw)

My picks are these (it’s also the contents so clicking the links will take you to that chapter). I’ll add a link each time I post a day, once all of them are complete it’s done.

Major themes are those listed below, anything else will be called out in the chapters top notes. As always mind the tags.

TL;DR a months worth of smut…

[Day 1 - Omorashi | Knifeplay | Body Swap - [Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/66623896)   
[Day 2 - Human Furniture | Sounding - [Liam/Theo]](https://archiveofourown.org/works/27269785/chapters/66629167)   
[Day 3 - Fisting | Medicalplay | Orgasm Denial - [Ethan/Jackson]](https://archiveofourown.org/works/27269785/chapters/66673930)   
[Day 4 - Incest | Breathplay | Leather/Latex - [Aiden/Ethan]](https://archiveofourown.org/works/27269785/chapters/66719821)   
[Day 5 - Spitroasting | Boot Worship | Lactation - [Derek/Jordan/Theo]](https://archiveofourown.org/works/27269785/chapters/66768007)   
[Day 6 - Free Use | Sensory Deprivation | Waxplay - [Derek/Stiles | Derek/Everyone]](https://archiveofourown.org/works/27269785/chapters/66791449)   
[Day 7 - Rimming | Breeding | Tentacles - [Derek/Theo/OMC]](https://archiveofourown.org/works/27269785/chapters/66849664)   
[Day 8 - Casting Couch | Bukkake - [Derek/Everyone]](https://archiveofourown.org/works/27269785/chapters/66876598)   
[Day 9 - Pegging | Emetophilia | Clone sex/Selfcest - [Stiles/Stiles]](https://archiveofourown.org/works/27269785/chapters/66890305)   
[Day 10 - Daddy Kink | Somnophilia - [Chris/Derek | Jordan/Noah]](https://archiveofourown.org/works/27269785/chapters/66899422)   
[Day 11 - Watersports | Temperature Play | Stockings - [Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/66935290)   
[Day 12 - Feet | Shotgunning (fist & reach around) | Dacryphilia - [Derek/Liam/Stiles/Theo]](https://archiveofourown.org/works/27269785/chapters/66944587)   
[Day 13 - Body Worship | Spanking | Frottage - [Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/66967060)   
[Day 14 - NTR/Cheating | Face-sitting | Collaring - [Derek/Theo | Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/66991282)   
[Day 15 - Prostitution | Armpit | Massage - [Derek/David Whittemore]](https://archiveofourown.org/works/27269785/chapters/67038637)   
[Day 16 - Fucking Machine | Feederism | Intercrural Sex - [Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/67059610)   
[Day 17 - Threesome/Orgy | Master/Slave | Titfucking - [Derek/Stiles | Derek/Everyone]](https://archiveofourown.org/works/27269785/chapters/67069645)   
[Day 18 - Petplay | Humiliation | Bloodplay - [Ethan/Jackson]](https://archiveofourown.org/works/27269785/chapters/67076386)   
[Day 19 - Hate Sex | Cockwarming | Mirror Sex - [Stiles/Theo]](https://archiveofourown.org/works/27269785/chapters/67085455)   
[Day 20 - Noncon/Dubcon | Foodplay | Creampie - [Liam/Theo | Liam/Stiles]](https://archiveofourown.org/works/27269785/chapters/67108756)   
[Day 21 - Size Difference | Exhibitionism/Voyeurism | Impact Play - [Corey/Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/67138630)   
[Day 22 - Formal Wear | Overstimulation | Sadomasochism - [Chris/Derek]](https://archiveofourown.org/works/27269785/chapters/67190674)   
[Day 23 - DP | Tickling | Shower Sex - [Danny/Ethan/Jackson]](https://archiveofourown.org/works/27269785/chapters/67237852)   
[Day 24 - Sweat | Branding | Masturbation - [Derek/OMC]](https://archiveofourown.org/works/27269785/chapters/67286500)   
[Day 25 - Bondage | Gunplay | Inflation - [Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/67332820)   
[Day 26 - Stripping | Scat | Burnplay - [Chris/Derek/Jordan]](https://archiveofourown.org/works/27269785/chapters/67379629)   
[Day 27 - Public Sex | Role Reversal | Xenophilia - [Derek/Stiles]](https://archiveofourown.org/works/27269785/chapters/67426324)   
[Day 28 - Crossdressing | Lingerie | Distention - [Derek/Liam/Stiles/Theo]](https://archiveofourown.org/works/27269785/chapters/67471900)   
[Day 29 - Praise Kink | Glory Hole | Telepathic Bonds - [Derek/Theo | Derek/Everyone]](https://archiveofourown.org/works/27269785/chapters/67510862)   
[Day 30 - Sex Toys | Deep Throating | Stuck In Wall - [Derek/Ethan/Jackson]](https://archiveofourown.org/works/27269785/chapters/67546642)   
[Day 31 - Free Day | Autofellatio | Bukkake - [Derek/Isaac | Derek/Everyone]](https://archiveofourown.org/works/27269785/chapters/67581800)


	2. Day 1 - Omorashi | Knifeplay | Body Swap

**Summary for the Chapter:**

> Derek and Stiles swap bodies, play with knifes, and have very full bladders.

**Notes for the Chapter:**

> Includes cutting and blood.

Derek could feel the palpable disappointment wafting of Stiles every time he shot down the idea; he just wasn't prepared to risk damaging him. Sure they'd done plenty of piss play before, but this went beyond that. And cutting into him? When he couldn't heal? Never. Then they found the book.

Stiles had dug it out of some estate sale for a dead warlock and thought it was a novelty until he began working through the incantations one by one and found they were real. It was creepy and weird and seemed to have more pages than something that size should fit. The leather binding was also of dubious provenance. Most of it was pretty evil magic, and they quickly came to the conclusion that the dead guy must have been a pretty nasty dude if he'd been using it — Stiles' words. Derek had never said dude in his life. That was his story, and he was sticking to it.

The spells that let Stiles steal Derek's healing abilities were the first ones they came across that came in handy. At least for their less than vanilla but always reasonably safe, relatively sane, and absolutely consensual sexual activities. But Derek still wasn't willing to go as far as Stiles wanted. Then they found the spell.

Luckily trust wasn't an issue for them by this point. Still, a spell called 'stealing the bodies of more powerful entities for use as the caster sees fit' would have sent Derek running only a year or two earlier. Now it made him wonder; would this be enough to let Stiles get what he wants?

It took a while for Derek to get used to a smaller thinner body that had just finished growing into itself. In his hands, well not so much his anymore, it still seemed to react like a baby giraffe. Stiles meanwhile seemed content to lie in bed, in his new two hundred pound frame of muscle and body hair, touching every inch of himself and marvelling at his new senses. The spell seemed to take a lot out of them, but less each time. Derek found it perverse that he was the one who had to cast it. Apparently, the cosmos deemed Stiles the 'more powerful entity'. After a few weeks, they had it down to an art. The casting took less than an hour. They could comfortably stay in each other's bodies until Derek chose to switch them back, and he wasn't tripping over his feet every second step.

They spent a week as each other and learned some exciting things. As it turned out, the ADHD was all Stiles, and he took it with him into Derek's body. At the end of that week, proof positive that it met Derek's stringent criteria for Stiles' safety they were ready to begin. Stiles could safeword out, and Derek would return to his body for the healing if necessary. He'd had far worse than what he was going to do to Stiles.

The next Saturday came, after two weeks living in one another's flesh. Stiles started drinking early and was regretting it by noon. Derek found it both arousing an incredibly weird watching what he couldn't help thinking of as his body. Hopping around the room in some bizarre pee dance it took swigs of water and repeated the mantra, 'I can hold it, I am the mighty wolf, roar, I will not pee on the rug.' They'd agreed beforehand that if Stiles couldn't hold it until nine in the evening, they'd start over the following day.

Eventually, the time came, and how Stiles had managed to hold it in Derek wasn't sure. Still, as he stripped off the henley, it became clear how swollen his belly was, rounded with all the piss he's built up through the day. Every movement was sheepish and drew a whine from his throat, so on the edge of losing control. It was surreal, watching Stiles in his body. Hearing it squeal when he couldn't help himself and pressed his hand against the bulging middle, seeing the glare he'd only ever seen in the mirror only now it was the wrong way round.

Stiles stripped off the rest of the clothes he was wearing, sobbing when he bent to push down the jeans and take off his socks. The uncut cock that was his, for now, jutted out, weeping and angry despite the pain he was in. It made Derek lick his lips. They'd cleared a space in the middle of the loft where Stiles now sat in a chair, rubbing circles into the dark hair of his swollen belly. A mess was to be expected here, but the concrete floor had already seen its share of bodily fluids, a few more pints wouldn't hurt it.

As the knife was brought out and the metallic scape against the sharpener rang out through the echoing space, Stiles began to press harder against his swollen bladder. Lightly he stroked the underside of his cock. His eyes were pained but hungry. Derek stepped forward and knelt in front of Stiles, momentarily distracted by the view. It was odd. He'd never been narcissistic. Now that his body was inhabited by Stiles, he couldn't take his eyes off of the hand moving along its dripping shaft or rubbing circles on its liquid-filled midriff. They agreed to it all over their weeks of planning. Derek would be clothed in what Stiles usually wore, jeans, tee, and plaid shirt. He'd start to cut, shallow slices, and press against Stiles' belly until he was crying. Again and again, he'd slice through flesh until Stiles couldn't hold it anymore.

'Ready,' Derek said more than asked, with his usual lack of intonation sounding off in a voice that wasn't really his. Running the flat of the blade along the inside of Stiles' thigh, making him jump from the cold and startling the first drops of urine from his hooded slit. The groan that accompanied it made his dick throb painfully in the tight confines of its Denim cage. 'Yeah, you're ready.'

As the flat of the hunting knife made its way down the soft flesh of Stiles inside thigh, Derek turned his wrist, and the blade bit into the skin a bead of red welling up behind. Slowly down it went, pressing in hard enough to turn the skin white before the blood rushed back to seep out of the shallow line that grew longer, inch after inch until the knife fell away at the bottom. Another dribble of liquid forced its way out of Stiles before he could control it.

Cut after cut, Derek sliced into Stiles, watching the blood well up, then wiping it away when the wound healed. Each time he revelled in his victim's growing loss of control, a little bit more piss dripped out, a little longer for the cut to heal. A nick to the back of the knee, a line from neck to navel, a gash to the groin, each one had Derek leaking into his jeans at the delicious sounds Stiles made while falling apart. When he sliced over a nipple, the noise Stiles had made nearly made Derek cum in his pants, and the spray of urine had been powerful enough to hit his face and shirt. With the taste on his lips, he wasted no time making another slice across the other one and decided Stiles should growl more often.

After a few slices to the veiny underside of the thick throbbing cock in front of him, and the warning that there wasn't long to go before Stiles couldn't hold it anymore, he climbed into Stiles lap. One hand went to Stiles' hair as the other brought the knife to his neck. Derek sucked at the exposed skin as his grip tightened and he pulled back, making sure to push his weight against the bladder which was ready to burst. As the knife began to press into the skin of Stiles' throat, he began to shake and sob, and as the red line opened up from one side to the other, he lost control.

Wet warmth began to spread through Derek's jeans, then spread up his shirt, and the heavy spray rose up between their chests. He began to grind down, starting his own flow in his pants, soaking them even more. His was concentrated enough for even the human nose he was currently sporting not having had to water down his bladder all day. Long before Stiles had finished his own stream rand out and he began to rut in earnest to bring them both off. Not until Derek's clothes were thoroughly soaked and a large puddle lay beneath them did Stiles flow cease. Its last dribble was followed by a powerful orgasm, and wet denim rubbed against him, cum hitting both of them in the chin.

How much time passed like that breathing hard and holding onto each other they didn't know.

'Shower?' Derek asked from his own body, placing a kiss on the corner of Stiles' mouth.

'Mmm,' was the mumbled response. 'I feel drained. Even though it was your body.' He shuffled in Derek's lap. 'And cold piss soaked denim isn't the most comfortable post-play clothing option.'

With no effort at all, Derek picked him up and carried him to the bathroom. They'd be doing this many more times. Maybe they could find some less evil and more enjoyable uses for the other spells in that creepy little book.


	3. Day 2 - Human Furniture | Sounding

**Summary for the Chapter:**

> Liam doesn't understand personal space and Theo likes to be useful.
> 
> Theo becomes Liam's footstool and Liam sounds his cock.
> 
> Dubious consent and under-negotioated kink.

Theo was more than grateful; Liam had convinced his parents to take him in. So thankful in fact, he didn't nip the invasions of his personal space in the bud. Shoving Liam's feet off his thigh as they sat watching a film the first time it happened would have been enough, but he didn't want to make a fuss. Now he was naked on Liam's bedroom floor, nose under Liam's musky balls sweaty from a challenging game of lacrosse.

He could pinpoint the moment it happened, that Liam realised Theo was his. After a few weeks of not pushing the feet from his lap, becoming accustomed to keeping Liam comfortable, Theo's attention had slipped.

'Dude, no, your feet stink.'

'Fine, whatever.'

Liam didn't move them. For some reason, it didn't occur to Theo to push them off. Instead, he turned to complain only to come up short when he was met with Liam's knowing smirk. That was also when he realised he was rubbing the stinking feet, pressing hard into the arches, massaging them. A split second after his dick throbbed and squeezed out a drop of precum he saw Liam's nostrils flare. To his surprise, Liam turned to sit facing forward on the couch and turned the TV on. Theo was bothered by how crushing the disappointment he felt was.

'Well? What are you waiting for, footstool,' Liam said, sneering. 'On the floor where you belong.'

Theo was down on the floor on his back, one sweaty sport sock pushing into his balls and rock hard pants-covered cock. The other was rubbing over his nose before he even questioned what the hell he was thinking. Liam didn't say anything to him just watched whatever crap was playing and messing on his' phone. Occasionally he moved his feet to another more comfortable position. For him, at least. Theo was pretty sure as disinterested as Liam was, his feet were aiming for the maximum level of discomfort for his footstool without putting himself out too much. Both feet crossed over, heel pressing into Theo's bladder was a revelation.

Liam still didn't say anything when got he a text from Mason, just got up and left, not even bothering to invite Theo along. Why would he? Who takes their footstool out to the movies? It didn't take long to open his pants, and only a couple of firm strokes had him shooting cum up to his chin. Not caring if he was going to get caught, he lay there for hours. No, it lay there for hours, just a discarded piece of furniture. Sometime after it began to get dark, but probably thankfully before the Dunbar's arrived home, a text came through from Liam.

{From Liam}

Footstool get you ass up to my bedroom and tidy it up. I want to come home to a clean floor and a naked stool under my desk for a CoD marathon. And I want snacks

{}

Now, months later, taking its place as a footstool while Liam leaned back in his desk chair, was as natural as breathing. It didn't even think about it, just moved into position when it heard it's owner making his way upstairs. Now Liam sat pumping a thick sound up and down his piss slit slowly stretching himself out. Theo's was plugged up of course, so it didn't dribble everywhere. For hours Liam would play with his big cock, stuffing it fuller and fuller until he couldn't take anymore and ripped the metal rod out, shooting cum all over his footstool. Tired and sated he'd kick his favourite piece of furniture under the bed, not worried about his cum staining it, and quickly fall asleep. 

It didn't fall asleep so quickly. The smell of its owners cum in its hair burned its nose. Dirty jocks and sweaty socks carelessly lost under the bed with it filling its thoughts until eventually, the reality of its new existence became too much. It came shaking and untouched, painful and too much with its piss hole plugged. Then it drifted off to sleep until it was needed again, wondering if Liam would ever share it with his packmates.


	4. Day 3 - Fisting | Medicalplay | Orgasm Denial

**Summary for the Chapter:**

> Jackson has an appointment with Nurse Steiner and it's a bit more in depth than he was expecting.

**Notes for the Chapter:**

> Fisting, Double Fisting, Deep Fisting, Paralysis, Medical Devices, Speculum, Orgasm Denial, Chastity

The quirk of the kanima that it could be paralysed by its own venom when in human form, came in quite handy when the new couple stumbled onto each other's kinks. How Ethan had managed to get the drip stand, saline bags, scrubs and various other pieces of paraphernalia, Jackson wasn't sure and didn't particularly care. Coming home to a gynaecologist chair being delivered was a head-scratcher though.

He couldn't help being nervous as Ethan watched him strip and the put on a hospital gown, much too small, his ass entirely on display as he turned. This was easy, but what came next would be new. At least part of it, the part that meant he couldn't get away, was truly reliant on Ethan to stop if he needed to.

'I'm Nurse Steiner. Come on, hurry up, you're late for your exam, and you're the last patient of the day,' Ethan said, sounding bored. If Jackson didn't know better, couldn't smell the arousal rolling off his boyfriend, he could have really believed he was just a bored nurse doing his job.

'Yeah, yeah, don't you have anything bigger than this,' Jackson said with a smirk as he walked over to the chair and his sexy nurse, then turned,' my ass is all hanging out.'

He'd hoped for a smack or a barbed response, but all he got was a border reply. 'It's nothing I haven't seen before, Sir. And I'm going to be looking inside your rectum, so covering it would defeat the object.'

Jackson felt himself blushing as though he'd just been chastised for flirting with an actual medical professional. Grumbling, he climbed into the gyno chair hooking his feet up into the stirrups. Immediately realising how exposed it made him, his cock began to fill with blood. Even though he wasn't thirsty swallowing felt like dry sand scraping down his throat.

Wheeling over the drip stand, Ethan took a set on a roller stool and let out a put upon sigh, and the thing gown began to tent. 'You're one of those ones then. Not to worry, I'll get you hooked up to the drip, and you'll relax, all of you, and you'll probably drift off to sleep.'

That wouldn't happen, Jackson knew, as the saline bag hanging from the drip stand would have a few drops of his venom injected into it. Slowly he'd lose control of his body and be unable to move, but he'd stay awake. They'd agreed from that point on how Ethan played it would be up to him. It heightened Jackson's nervous state, but that was the whole point.

'Sharp scratch,' came the only warning before the needle pressed into the back of his hand and was taped down. He let out a hiss but nothing more. The saline began to flow, a slow regular drip that Jackson focused on to calm himself. He'd never, ever trusted anyone this much before. 'Okay, here we go,' Ethan said, a syringe in his hand filled with a clear liquid, slightly tinted with yellow. 'Are you ready?'

That was it; part of the scene and Jackson's last chance to back out under his own power. Once he said yes, he wouldn't be able to speak or transform. Only his eyes would tell Ethan he'd had too much and he'd have to trust that the signal would be received and acted on. He nodded. 'I've been waiting for weeks for this appointment. Get in with it, I've got plans tonight.' He wasn't expecting the nasty grin on the nurses face as the plunger went in on the syringe and the liquid began to mix with the saline.

'Oh, you won't be going anywhere tonight, Mr Whittemore. I've been looking forward to this for a long time, and I'm not letting you go anywhere until you've been very thoroughly examined.' Black nitrile gloves were snapped into place, and then a large speculum which Jackson was almost certain wasn't designed for humans came into view. He wanted to say something, but he couldn't move his mouth. Already he'd been paralysed by the venom flowing directly into his veins.

'First I'm going to open you up and take a look inside,' Nurse Steiner said. Jackson couldn't bring himself to think of him as Ethan anymore and that both terrified and aroused him. Slowly the long piece of steel was slicked up with lubricant the without warning a gloved finger pushed inside his hole. The sensation was bizarre, he could feel everything, could feel his muscle tight against it, but it didn't clench down. When the finger was removed, his hole didn't tighten straight away. It stayed open for a few seconds before it seemed to close under its own weight rather than muscle contraction.

'That's a good response,' the nurse said, poking around the hole, 'when we open you up properly, you should stay stretched out for quite a while.' This time two fingers pushed inside to the root then hooked upwards to press against his prostate. As they rubbed and pressed, feeling around inside, Jackson wanted to push it out, yell for more, for harder, beg to be fucked, but he couldn't; he couldn't even moan or cry.

For what seemed like hours, the fingers rubbed against him until he felt the sensation of an orgasm building and then wash over him like a bucket of ice-cold water. Nothing. No cum, not muscle contractions, just a dribble of something wetting the paper gown where the tip of his now soft cock lay and another positively evil grin from the nurse. 'Oh, that's perfect, Mr Whittemore, I don't even have to be careful about it. Nothing's going to make you ejaculate as long as your hooked up to the paralytic. I'm sure you were expecting a tranquilliser, but I find this makes for a much more personal experience.'

Slowly the cold steel of the speculum began to slide smoothly inside Jackson's ass as Nurse Steiner continued. 'It's a special blend, might not work on an elephant, but I know a vet that works with dangerous animals, he uses it to make them relax. Even alpha wolves. Now you get to experience it, Mr Whittemore.' The handle sliding into place and butting against his perineum should have made him jump. All Jackson could do was watch on feeling everything but as though watching someone else.

Each click of the ratchet opened the speculum out wider, opened him out wider. Every couple of clicks the nurse would stop, massage the stretched-out rim of his hole and shine a torch inside. 'Not yet,' was mumbled each time, but the nurse kept his heads bent down, focused on his task. Until after a few minutes when Jackson thought maybe he'd rip in half, a joyful shout of, 'ah-ha!' Nurse Steiner popped his head back up, a happy toothy smile; too toothy. A hungry smile. 'There we go, you made it all the way Mr Whittemore. Quite the achievement. You have a very flexible sphincter. I wasn't sure you'd get all the way, but there you are, dilated to five inches.'

That was impossible. Jackson wasn't small, but his dick was only an inch and a bit longer than that. How the hell had his ass stretched out that far. He could feel himself start to panic, and his visions swam, then he felt warm hands on his thighs. Gloveless now, they stroked slowly up and down, and he focused his eyes back on his sexy nurse. 'You're back. Okay, Mr Whittemore? We both know you need this and you're doing so well, you've stretched out beautifully, and I think we should finish your examination.' Jackson blinked, he couldn't control it so he couldn't use it to communicate, but something passed between them, and Ethan sat back.

Once again, Ethan faded away, and Nurse Steiner returned with longer gloves which he rolled on, down past his elbows. This time they were coated with something thick and white. Jackson's heart beat faster as he realised they were going to go so deep inside him, though there was no external sign to show how much it excited him. Each touch now came with a running commentary, clinical and emotionless.

'First I'm going to coat your anus and inside your rectum with lubricating cream,' Nurse Steiner said. At the same time, he began to run the grease around Jackson's paralysed hole. Then his hand began to push forward, massaging it into the walls Jackson's insides. Once he deemed the job sufficiently done, he started to burrow in further coming to a blockage a few inches inside. 'That's the bend in your bowel, moving from your rectum to your sigmoid colon.' Seemingly to prove his point, he pushed through it with a couple of fingers before moving back. If Jackson had been able to move, he would have shot off the chair bucking his hips up into the air, it felt so incredibly full. 'But for now, that's as far as we go. Part of the exam will see how deep you can take an object, but first I think we need to get that speculum out and then have a good feel around in there, make sure nothing's too out of place.'

Without any further warning, the catch on the steel jaws holding him open was released. Jackson expected his hole to snap back closed around the nurse's arm, but it didn't. Like that first stretch, the paralytic venom running through his blood kept him gaped wide open closing ever so slowly as the muscle couldn't hold up under its weight. The arm of the nurse that wasn't buried inside him was pulling the device out slowly, and when it cleared his rim, he realised that the one still inside him wasn't even touching his hole.

'Amazing Mr Whittemore,' Nurse Steiner said, unable to keep the awe out of his voice even though he kept his face passive. 'Barely closing up at all and wider enough you're sphincter isn't coming into contact with my arm. We'll try some two-arm technique for the inspection as you're so open, then move on to the depth portion.'

The other gloved arm began to slide inside him alongside the first, and Jackson felt that same non-orgasm approach again as knuckles pressed into his prostate once more. This time knowing what to expect, he just relaxed into it and let it wash over him. The sensations lasted longer this time. They built as his nurse moved their arms over each other, in and out in constant movements, pressing into the walls of his rectum and adding just a little bit of new stretch to his gaping hole. Jackson could feel the tears slowly dripping down his face from the dual feelings of immense pleasure, pressure, and frustration.

'Remarkably responsive, despite the paralytic, Mr Whittemore, I'm impressed. You should volunteer for a teaching hospital, let all those student medics get their hands inside you and feel around.' The arms moving inside him began to work their way to a greater depth. The grin on the nurse's face gave away his enjoyment of the torture he was inflicting on his patient. One of the hands slipped back and the other pushed through, rounded the bend and going deep inside Jackson and making his eyes roll back into his head. 'That's it, Mr Whittemore, it's through now, pushing into your sigmoid. We'll see how far we can get. Don't worry though, if there's an obstruction that stops me checking you up to my elbow we'll give you some exercises and a diet sheet for you to work on at home, and we'll try again next time. In no time you'll be ready to complete the full exam and let me in all the way up to my armpit.'

Jackson was barely able to follow what was being said. As the arm so deep inside him moved deeper still, then pulled out in a long smooth movement only to be replaced with the other pushing in even further into his core thoughts weren't really possible. The first time he felt an elbow pulling back against his stretched out hole, he twitched around it. With difficulty, his head lifted to see it moving inside him better.

'That's it Mr Whittemore,' the nurse sing-songed, 'we're nearly there now just the last part of the exam to go.' The hand that wasn't buried deep inside him began to slowly pump at his gown covered cock, and Jackson let out a plaintive whine. Slowly his hips began to buck up into the dual sensations of a slick glove and a full cunt. Too late, he realised that the drip had been stopped, that he was regaining control of his body. Nurse Steiner timed it to perfections. Just as Jackson began to slowly move his arms towards his crotch, the arm inside him pulled out, and the one stroking him fell away.

'Excellent responses. You're recovering from the paralysis as expected. Your sphincter is closing up nicely. I am worried about the swelling here though.' With that came a poke to Jackson's cock and he let out a growl now he knew he could. 'Yes, I don't like the swelling in your penis. I think we should do something about that, don't you, Mr Whittemore?'

'Yes, fucking yes!' he roared, misunderstanding what was being proposed. He begged and cried, but he still didn't have the motor control or strength to do a damn thing about it. Seconds later he'd been squashed down into a solid chastity cage, with only a hole for him to piss through. It was steel, and he probably wouldn't be able to break it off without damaging himself. Even with his healing, it wasn't an area he was eager to damage.

'There we go, all sorted. Compression is the best thing for swelling. That should probably stay on until your next appointment,' Nurse Steiner said as he ripped off his long gloves and replaced them again with the normal black ones. He began to wipe Jackson clean of all the mess dripping from him. 'How's next Thursday?'

'I can't make next Thursday,' Jackson mumbled, worn out and so ready to be taken further into this submissive state. 'What about the week after?' He could manage two weeks, surely? Pissed off as he was that he didn't see the cock cage coming.

'I'm sorry, Mr Whitmore, but this is a busy time of year, and for obvious reasons, I think you can understand why I need you to be my last patient. When everyone else has gone home, we can home a good long look at you without any interruptions. It's next week or at the end of next month. We'll see you before then, of course, to let you out for cleaning every couple of days, after an application of a paralytic to the affected area. We wouldn't want any accidents now would we?'

Fuck. Five weeks. Five weeks locked up in this tiny little cage, only let out for cleaning after slathering his cock in venom so he couldn't even whack one out in the shower when he wasn't being watched. Five weeks of complete and utter submission to Ethan. Five weeks of torturous bliss. 'Five weeks sounds perfect,' he moaned.

'I can't wait, Mr Whittemore, it's always a pleasure to perform your procedures.'

'No one's ever bought me a gyno exam chair and paralysed me for my birthday before,' Jackson said, then thought how stupid it sounded because of course, they hadn't.

Ethan understood through. 'Only the best for you, babe. You're my favourite patient.'

'Mmm,' Jackson mumbled beginning to drift off. 'Love you, Nurse Steiner.'

'Love you too, Mr Whittemore,' Ethan replied with a grin. 'Love you too.'


	5. Day 4 - Incest | Breathplay | Leather/Latex

**Summary for the Chapter:**

> Aiden and Ethan have some sibling breathplay and dress up for the occasion.

**Notes for the Chapter:**

> Incest, breath play, choking, unconsciousness, oxygen deprivation, coming untouched, breeding.
> 
> Includes allusions to thoughts of death and shame. Not, however, suicidal ideation.

Ethan adores rubber and Aiden's partial to leather. Ethen doesn't care what the belt wrapped around his neck is made of, as long as Aiden keeps pulling it tighter. As long as his twin keeps fucking into him with long slow strokes, driving him insane.

All of Ethan was covered, head to toe, the only holes in the latex gimp suit for his nostrils and a rubber ring giving access to his asshole. It was a nightmare to get on or off, but he loved how it cut off his ability to see what was happening around him; loved when he began to sweat and itch. He'd never seen what Aiden changed into as it always happened after his vision cut off. But he could smell the leather. He could feel the straps of the harness crossing over the hard muscle of Aiden's chest through the thin rubber of his gloves.

Each time was the same. Lying back on the bed, legs hiked up around Aiden's waist, Ethan would grab hold and pull his brother closer. Hands would roam his rubberised body, and then the day's ligature of choice was wrapped around his neck. It was usually a belt, that seemed to be what Aiden favoured. Between them, they had an assortment of leather and fabric ones; the couple made from thick black rubber were Ethan's.

The tighter it became the harder his brother's cock would get against the second skin over his ass until finally, it would push inside through the gap in the suit. Vision beginning to swim with bright popping lights inside his pitch-black confinement let Ethan know the belt was doing its job. His oxygen depleting caused the sensations lower down to power into overdrive. Slowly Aiden's cock sawed in and out, burying itself to the hilt and withdrawing until the tip kissed the opened rim. The pace never changed.

An aficionado of extreme breath play, Ethan could hold his breath a long time. Still, it always seems like he was being taken to pieces for hours, despite the belt only ever getting tighter, no extra air seeping in. It would reach the point that his body refused him control and began to fight against his wishes. By then, it was too late. His arms might manage to flail ineffectually towards his neck or hips bucking weakly with no chance of throwing off his brother.

Calm washed over him as the dancing lights went black. One by one, he would feel his muscles relax like they were getting into the inevitable. Giving up. Pleasant. It was the only way to describe it. The cock sawing into his hole felt like a hammer hitting an anvil as all sensation focused there and then travelled up. Always last, with perfect timing, contractions began. Squirt after squire, his cum oozed from his untouched cock held in place, pointing towards his chest, in its rubber prison.

Then nothing.

There was no more sensation, no more feeling. Ethan always thought that it felt like he was floating in an endless void. Though, perhaps that was only what his mind filled in when he awoke. If the belt kept tightening, if too malevolent a thought flashed into being, if Aiden took too long to finish; then what? Would he float in the void forever, or would he feel nothing?

Waking up to a darkened room, pleasantly aching, neck sore, hole dripping with fresh cum, he asked himself these questions. Maybe he'd ask Aiden if he stayed. Never. Though, each time, he left the belt, rolled up, so Ethan knew which one had been picked. Rubber, black, polished, and a quarter-inch thick. Ethan's favourite. It was how he knew Aiden loved him, even though he couldn't face this looking into his twin's eyes.


	6. Day 5 - Spitroasting | Boot Worship | Lactation

**Summary for the Chapter:**

> Theo has some side effects of his chimerism which have gotten stronger every year. Last time he got through it with a dildo and a breast pump but this time he can’t shake his big brothers. Turns out when Derek and Jordan get a whiff of his milk and slick, they’re more than willing to let him lick their boots and fuck him through it, draining his swollen tits while they rest for round 2.

**Notes for the Chapter:**

> Main themes per the prompt spit-roasting, boot worship, and lactation (male).
> 
> Whilst everyone is consenting to everything in the moment, there's a distinctly sex-pollen/monsters made them do it feel to this that some might consider dubcon, if not outright noncon. If that's a problem for you I recommend skipping this chapter. Possibly could be considered body horror based on the changes Theo goes through.
> 
> Cock shrinking, self-lubricating, pheromone leaking, male in heat.
> 
> Also, this one really got away from me and is 3-4 times longer than I was planning any of these Kinktober prompt pieces to be. The fact it poured out so easily and wouldn't stop has me thinking of spinning this off into its own longer piece. I've even written the makings of a prequel and sequel into it!
> 
> Enjoy ;)

They raced through the forest, chasing down the scent of panic and shame. For the last couple of years, Theo had been acting weird around the blue moon, getting irritable and cranky before disappearing for a couple of days.

After a few miles, they lost the scent where it began to take on the whiff of fear. Derek was so concerned they nearly called in the cavalry before picking it up again. The weirdness had started to show itself during regular full moons though to a lesser extent, that the rest of the pack put down to usual wolfy behaviour. Sometimes they forgot the chimaera wasn't affected in the same way.

It seemed like the route had been laid out intentionally to put off trackers. Set by someone who either wasn't thinking clearly or who didn't know much about a dogs ability to track, let alone a werewolf. Despite the long circuitous route through the preserve, they were coming to the opposite edge. They could have made a straight line in a tenth of the distance. There were cabins there, secluded and cheap to rent at this time of year. As this blue moon had approached Theo was acting weirder than usual; becoming upset at the oddest things, always flinching from the male pack members, cosying up to the women. Spending a significant amount of time with the pack associated mothers. It wasn't that there was anything wrong with these things, they were just out of character for Theo.

As they broke through the trees to the dirt path which connected the dozen or so summer cabins, each spaced about a mile apart they were his with a new component to the scent trail. They'd expected wolfsbane or some poisonous ichor, but not this.

'Holy fuck,' Jordan wheezed out. A sweet, cloying wall of scent surrounded them in the open air. It was making his mouth water, his heart race, and his cock… 'Derek,' he mumbled sheepishly. 'Is it just me, or…'

Derek interrupted, 'am I hard as a rock and leaking through my jeans?'

Jordan blushed but nodded. 'Yeah,' he coughed out. 'Is it? You don't think it could be a succubus, do you? I remember Stiles' lecture before they all went off to college. Sweet, enticing smell?'

'No,' Derek replied, setting off again at a walk this time, but no less purposefully. 'I've met a succubus and her incubus brother. Weirdest implementation of protective older brother ever. But they smell of whatever you desire. Stiles just thinks they smell sweet because he mainlines overpriced coffees that are mostly syrup.' He snorted in derision. Derek owned a costly Italian machine. His eyebrow twitched whenever he opened the cupboard containing a bag of Hawaiian Blue to find it also housed butterscotch syrup and powdered creamer. 'This is cloying, heady, it's like…'

Jordan nearly walked into Derek's back as he stopped mid-stride and mid-sentence suddenly. 'Smells like what?'

With some mix of concern, confusion, and what might have been fascinated awe, slowly Derek turned his head to look at Jordan. 'Like a bitch in heat.'

That was not what he was expecting. 'Theo's with a dog?' he asked, confused.

'No. There's no smell of dog. It's just Theo, all Theo.'

'Then, what? Theo's in heat? That's absurd. Werewolves don't go into heat. Do they?'

A shake of the head. Then, 'no. But he's not a werewolf, is he? Even he doesn't really know what he is, what he's made up of.'

As they resumed their search, slower, more relaxed now at least they were sure Theo was at least safe, they both lost themselves in thought. After they'd each caught the other groping themselves in some ineffectual attempt at surreptitious adjustment half a dozen times by unspoken mutual agreement they sped back up to a run.

'Are we perverts?' Jordan asked after a few minutes, the slightest hint of exertion in his voice.

'Because we're getting hard from the smell?'

'Because we're still running towards it. Even though we know what that probably means.'

Derek didn't look at him when he finally answered a couple of minutes later. 'Yeah. Probably. But I really don't care.'

Eventually, they passed the second to last dark empty cabin, and the smell grew even headier as they closed in the last few hundred yards. Theo was in the final building, they were sure about that now. They were t sure about what was going to happen when they went inside, as much as their dicks seemed to disagree. Jordan's hearing wasn't as acute, but even he could hear the wails of anguish as they approached the door. To Derek, every hitched breath, every gasp was audible. He listened to the frantic rubbing of dry skin on skin and the squelching of fingers desperately sinking into wet heat. The door wasn't locked. They went inside. A humid fog of pheromones awaited them.

Despite himself and his attempts to remain in control, Derek knew his face had shifted with eyes burning amber. Only Jordan's hand reaching out to grasp his own kept him grounded enough to keep his claws retracted and prevented him from pouncing. He squeezed back in thanks and his own silent support. The cabin was simple with a bed, dresser, en suite bathroom and small kitchenette. The door to the bathroom was open, but no one was inside.

'You need to leave, please,' a voice from behind the dresser near the window sounded. In the small space between the piece of rickety furniture and the bare wooden wall hid its source, evidenced only by the pair of bare feet sticking out.

'We won't do that, you need help.' Derek took another step into the room, not releasing the grip on the hand in his. A choked off sob followed, and he stilled. 'We won't hurt you, Theo. We won't make you do anything you don't want to. But we won't leave you like this.'

'It's not me I'm worried about. You smell so good,' Theo croaked. 'And I'm so hungry; so empty. Too full. I need…I don't know what I'll do if you don't go now. I won't be able to stop myself. And I think I might make you do things you'll regret.'

Taking another few steps, Jordan following at his side, more of Theo's legs came into view. 'I don't know why it's happening, but I think I know what's happening to you. And we want to help. Please come out'.

Slowly a naked body crawled forward before rising shakily on unsteady legs. Theo was a hot mess. Face streaked with tears and blotchy with redness, it looked like he'd been crying in a sauna for the last few hours. His hair was soaked with sweat. The mottled blush spread further down, but that was where things took a turn for the supernaturally absurd. Swollen to twice their usual size, his pecs had gone from hard muscle to soft pillows, filled with fluid; not breasts, still in their old shape, just more massive and more delicate. The areolas had doubled in size. The nipples, firm and an angry red, were the size of the end of a pinky. A slow constant ooze of creamy off-white liquid was running in thin rivulets down his midriff to what perhaps were the most startling changes.

'You need help Theo, and if you don't want it from us, we need to get your to Deaton.'

'No!' The refusal was emphatic. 'I don't trust him...isn't pack'.

Derek had seen Theo naked before; most of the pack, in fact. It was a consequence of being a supernatural social creature. In passing, he'd noted a respectable above-average piece of meat hanging between Theo's legs that he'd filed away and not really thought much more about. Now though, it was barely two inches long and hard as a nail, sticking out at a slightly upwards angle and looking even more painful than the nipples had. What made Derek and Jordan exchange glances though, was that it was dry. The pungent smell of slick they'd been chasing down wasn't coming from the tip of his dick. Instead, it seeped down from the back of his balls, in between his legs, from his ass. In the look they shared, they saw the same guilty thought in each other's eyes as their dicks twitched. No matter how unpleasant this was for Theo, no matter how pitiful he looked, they were both turned on beyond belief by it. And, no matter what, they were going to do everything in their power to help him through it.

'Come here, baby,' Jordan cooed, holding open his arm in an invitation, taking the initiative from a stalled and stunned Derek. Theo stumbled forward into their waiting arms and was wrapped up in between them. His skin was burning, and he shook as he searched for any exposed skin to rub himself against.

'Wow,' he said, sounding more lucid. 'I can't believe how much that helped, just touching you.'

'What do you need, baby? Tell us what you need from us. What do you normally do when this happens?'

Theo gasped, realising that they knew this wasn't the first time. 'I…I can feel myself slipping again; it's not enough.'

'Tell us,' Derek ordered with a growl.

Theo squealed. 'That! I need it. Make me yours, make me know my place, make me take it to make me…make me your…,' he trailed off.

'Bitch!' It was both a confirmation and a claim from Derek.

'Yes,' hissed, Theo. 'I usually fuck myself with a dildo, rub myself raw 'till I've cum half a dozen times and it takes the edge off enough I can use a breast pump on myself. But this time…fuck this is so humiliating. My dicks gotten so small I can't even jerk off. I was frustrated, tried to get the pump on anyway, ended up with my claws out shredding the tube. My ass is so fucking wet I can't even get the dildo in it keeps slipping.'

'Show us that you're our bitch, baby. Get down on your knees and beg us to give you the relief you crave.' Jordan sounded so soft and sweet compared to Derek's gruff dominating commands. Still, only a fool world have missed the authoritative edge to his voice. Theo sank down to the floor.

What he did next still came as a surprise, but it gave them a moment to get their bearings. Instead of having their pants opened, and cocks pulled out, their new bitch dropped right down. He began making little kitten licks at the toes of their boots before taking longer more purposeful swipes, searching out any dry patch of leather. Moving at the same time, mouths crashing together, Derek and Jordan worked frantically to divest each other of their jackets. Then, reluctantly, pulled apart long enough to strip their shirts. Bare-chested and mouths connected again, they shuffled towards the bed and fell to sit in the edge side by side.

Belatedly they realised Theo had been crawling along behind them. Trying not to lose contact with a booted foot and letting out whimpers if he lost the taste of leather and spit on his tongue. Derek groaned, rubbing his cock through his jeans. 'Such a need fucking bitch, licking our boots like he belongs there.' A grin spread across his face as an idea struck. Voice saccharine sweet with false gentleness he asked, 'You like the taste of dirty leather, bitch?' Without stopping, Theo turned his head to look Derek in the eyes and nodded. His pupils were the size of saucers. 'Get on your back, bitch,' Derek said, returning to his growl and reinforcing the order with a light kick to the bitches ribs.

Theo did as he was commanded and began to groan and hip the air when the sole of Derek's boot landed on his face. He wasted no time darting out his tongue. Seemingly without caring that they'd been running through the woods, Theo began to lick and suck the rubber soles, diving into the deep treads. Jordan wasn't idle at the sight, though he decided to indulge Theo's love of boots in a different way. The sound that came out of the bitches mouth was a high pitched gurgled scream at the sudden sensation of a booted foot grinding down onto first one, then the other swollen and leaking teat.

Derek gave up his position at Theo's head to allow Jordan's boots to be cleaned of the milk staining their soles and moved between legs which began to draw up and out. It was like Theo could sense a dominant male seeking entry to his slick hole. As the sight of the damp, sticky rim came into view, the steel-capped toes of Derek's left boot pressed in, and the reaction was instant. Under the boot on his face, Theo released a scream, and his hips began to pump into empty air, seeking friction. Not once did he bring his hands up to touch any part of himself, trusting himself now to their hands. Removing his boot from the heat to find it soaked and dripping with the slippery, viscous liquid, Derek paused for a moment in awe. Then, with a nasty grin aimed Jordan's way, ground his boot down. Down onto the swollen balls and painfully hard micro-cock, Theo's spread legs invited sleazy access too. A groan began to spill out from under Jordan's boot, hips thrust up violently once, twice, the Derek twisted his foot. Theo's moan turned to a high pitched squeal that seemed to go on forever, and his body began to shake violently. If it weren't for the thin cloudy liquid pumping out onto his belly as he spasmed, Derek might have thought he'd broken Theo. More than a pint of the watery cum pumped out of him by the time he stopped shaking, and Derek's boot let up its pressure.

As Theo's heavy panting came back under control, Derek and Jordan returned to their perch in the edge of the bed, giving him a moment to compose. Soon enough he was up on all fours again, licking his mess from Derek's boot; efficient and perfunctory. The need to move on clear, despite seeming to love the feel of the boot under his tongue. 'Thank you. It hurts less now, the burn's not as bad. But,' he began before kneeling up and started to remove their boots, socks, and loosening their pants. 'But I need to be milked. You'll help with that too, won't you? I know it's weird.'

Both men ran a hand through Theo's hair and the sides of his face revelling in him leaning into the petting. 'Get settled on the bed,' Jordan said softly.' Prop yourself up a bit in the pillows.' He then stools, pulling Derek with him, and they shucked their pants. Jordan wore trunks for comfort. He couldn't help snorting at the blush on Derek's face as white lace panties came into view, obscenely bulging and juxtaposed with the dark hair of his belly and thighs.

'They're comfortable,' defended Derek.

'Uh-huh,' was the unconvinced reply. 'We can come back to that. Don't think I'll forget it. But now, we should get over there and drink him dry then fuck him to exhaustion.'

They stripped their underwear and moved to the bed, each taking a side of Theo, heads resting on his chest and hard cocks nudging into his thighs. Derek brought his hand up and pinched the nipple he'd claimed. Liquid shot out a foot into the air before splashing back down. 'Fuck,' he groaned.

'Please,' Theo begged. It was all the encouragement they needed. Each took a swollen leaking nipple into their mouth and began to suckle. Their mouths were filled with sweet, warm milk, smooth and creamy and tasting so, so good. It was addictive. They drank and drank until they felt over full. Theo's chest had shrunk back down to something approaching his usual size, and the flow was slowing to a trickle.

Pulling off with a pop, they look at each other's messy faces, stained with white, in Derek's case dripping from his beard. They met in a sloppy kiss tongues delving into mouths and along jaws seeking out more of the taste. A moan from Theo realigned their attention, and they began to claim his mouth, sucking on his neck, drawing out mewls of pleasure.

'I think you need breeding now don't you, bitch?' Derek asked.

'Oooh yes!'

'Taking one of us down your throat, the other in your dripping cunt, fucking another orgasm out of you.'

'We'll let you chose who gets which end the first time.'

Jordan coughed, drawing their attention. ‘Er, Derek, do werewolves knot?'

Snorting in derision, Derek replied, 'no. Is that from another of Stiles' lectures?'

'No. I just wondered… 'cause hell hounds? We can.' At that, Derek's eyebrows climbed, and he licked his lips. Jordan filed that away in the same part of his mind as the tight lacy panties.

'Yes,' Theo hissed. 'Please, Derek, let him fill my cunt with his knot. You can fuck it whenever you want, but I need it now. Please?'

Nodding, Derek replied, 'okay. Hands and knees. We're going to breed you like a real bitch in heat, doggy style.'

Theo didn't waste any time, scrambling into position on his hands and knees across the twin bed. Ass in the air and back arched he swayed from side to side, inviting Jordan to stand and sink into him. They'd both been hard and dripping for hours by this point and weren't in the mood to waste time on pleasantries. Jordan stuck three fingers into Theo's cunt, meeting very little resistance, to scoop up some of the thick sticky liquid and then lubed up his dick with two quick strokes. Despite the mess at Theo's rear looking like one of those videos of someone trying to handle a hagfish, he wasn't at all put-off. In fact, it spurred him on, and without warning sank all nine inches of all American cut cock into the waiting heat.

'Oh fuck,' Jordan moaned out as Theo started up a subvocal drone which seemed to keep sounding regardless of whether he was breathing in or out. 'It's so warm and wet and tight. Like the perfect cross between pussy and ass.' Slowly he began to thrust in and out, building up speed. The faster he went, the harder his hips bashed into Theo's plump ass with a reverberating slap, the higher-pitched the bitch's noises went.

For those couple of moments, Derek was content to watch, but his own cock had been similarly deprived of attention for far too long. Taking up his place at the other end, Theo lazily lifted his head to come eye to eye with a thick juicy uncut piece of meat. His nostrils were flaring from the scent and drool was beginning to fall down his chin, but he didn't make a move, waiting for Derek to use him as he wanted. 'Open up, tongue out,' Derek ordered, and Theo instantly complied. 'Don't lose a drop and take a deep breath, bitch.' With that, Derek peeled back the foreskin covering the head of his cock and releasing the floodgates on the reservoir of built-up precum. Theo craned his neck forward and strained as far as he could to drink down the nectar and suckle the purple mushroom head, restricted as he was. Strong hands digging into his hips, pulling him back onto the cock that was rearranging his insides kept him from surging to far forwards.

Bolder after a few seconds, Derek took hold of Theo by the back of the head. Thumbs pressed to the rear of his ears as leverage, Derek leaned forward and slowly pushed inside until he had buried himself to the hilt in one long smooth slide. A skilled throat, whether through bizarre biology or promiscuous experience, fluttered and squeezed around him. He even felt a tongue squeezing out to lick at his balls. He began to thrust, building up speed, testing and careful not to harm their bitch. It soon became apparent that Theo was more than capable of taking the punishment; was made for it in fact.

Determined to hold out until Jordan had at least popped his knot, Derek was sweating profusely desperately staving off his release. Then, Theo began to choke and splutter, Jordan's eyes rolled back, the unmistakable popping squelch of something forcing itself in and out of the bitch's rim. One last thrust, Jordan slammed in, shaking and Theo screamed around Derek's cock. It tipped him over the edge, and he began to shoot, rope after rope of cum. Starting in the tight throat then pulling back to feel a tongue swiping at his oversensitive slit. Spurt after spurt it spat out, a bitter, salty liquid that Theo couldn't get enough of. Eventually, he had to pull out with a whimper, too much even for him. He had the chance for a moment, to sink his tongue inside and taste himself before Theo was ripped away.

Jordan pulled Theo up to his chest and climbed on to the bed, hiking up a leg and twisting Theo on his knot, so that a milky nipple came in reach of his searching mouth. It was obscene. Derek could see where they were tied, could see the rhythmic pumping of Jordan's balls and the bit of shaft beneath where the knot was formed, spilling vast amounts of cum inside. When Theo began to cum again from the sensations, Derek dived onto the hard little nail. Sucking hard, he gulped the thin liquid down and smiling, wondering whether calling it a pretty little clitty would be appreciated.

Once the flow stopped, and the little mewls from Theo took on the edge of oversensitivity, Derek released his small mouthful. He trailed kisses up Theo's belly before sharing a milky kiss with Jordan, then latching on to a nipple of his own and snuggling into the free side. To his surprise, Theo's chest had swollen back up to the size it had been before they had started. They suckled until the knot had shrunk sufficiently to pop in and out on its own with their heavy breathing, and the smell of Jordan's leaking cum filled the room. Theo's chest had barely shrunk.

'I'm so full,' Derek moaned rubbing his belly, distended from its usual washboard flatness by a gallon of sweet, creamy milk.

'Me too.' Jordan's reply was reluctant, not wanting to pull off of Theo's red and swollen nipple.

'I suppose we could keep helping Theo through these heats, taking the edge off. But look at him, Jordan, his tits are swelling up faster than we can drain them. There's only so much the two of us can do,' Derek sighed, winking at Jordan.

'You're right. If only there was something more we could do,' said Jordan grinding his still semi-swollen hellhound knot into Theo's prostate at the same time. Their scheming was rewarded with an encouraging moan begging for their help. 'Wait, Derek, we're so stupid!' He continued, not even bothering to hide the shit-eating grin from his voice anymore. Theo was only just taking in their words, following the context was beyond him. 'If the two of us aren't enough to fuck Theo through this and drink him dry…'

Where Jordan finished, Derek picked up, as though he'd just realised. 'Of course! The pack can all help. All those mouths sucking on his swollen tits, big cocks pounding his holes and filling him to the brim with cum! Theo that's it, we'll call in the pack to help.'

In the back of his heat addled mind, Theo was vaguely aware that he hadn't wanted anyone to find out about this. The embarrassment and shame still simmered, but the burning desire to sate his hunger was overwhelming relational thought. It wasn't that he didn't want to be bred and milked by all the pack's studs, he just thought they'd find the whole situation, him, disgusting. Now his needs overrode his concern as the hot fibrous knot of flesh stretched out his dripping hole. The mouth of his big pack brothers each latched onto a milk swollen teat, all he could do was beg, enthusiastic in his agreement. 'Please, yes! I need them all.' A phone unlocked and the tapping of the screen sounded, then a message sent. Soon after, one by one replies began to chime.

Derek smiled up at Theo, leaned in to plant a kiss on his mouth and before going back to suckle once more comforted the twitching chimaera. 'Not long now, Theo, then they'll all get to use you. They're so excited to meet the new pack bitch.'

Eyes rolling back, his body began to spasm as he started the strongest yet of these new endless orgasms, spraying up to soak the faces of the suckling men.


	7. Day 6 - Free Use | Sensory Deprivation | Waxplay

**Summary for the Chapter:**

> Derek agrees to be Stiles free use stress relief and the next day doesn’t think anything about it when Stiles comes over with the duffel with sensory deprivation kit and candles. Then he remembers what he agreed to. Not that Stiles could use him whenever he wanted but that he could be used whenever Stiles wanted.

**Notes for the Chapter:**

> Free Use, Sensory Deprivation, Wax Play, Breeding, Blow Jobs, Orgy
> 
> Possible dubcon as Derek is giving away the need to seek his consent, and doesn't fully understand what he is consenting too when he does this, though he is offered an out and refuses it. If consent issues are problematic for you, you may which to skip this chapter.

'Derek?'

An eyebrow raised in acknowledgement but otherwise nothing.

'Why do you never say no?' Stiles mused.

A sigh. A realisation this was going to keep going until Stiles got the answer he wanted. 'No to what.' It wasn't a question. Never a question, like his voice didn't understand how that intonation worked.

'No to sex.'

That wasn't what he expected. 'I've said no to sex.'

'Not to me.'

'You want me to say no to you.' Derek was confused.

'Hell no. Just...sometimes I feel like you're not really into it, but you never say no. And, I can't help feeling like I'm doing something I shouldn't.'

'Oh.' Derek put his book down. 'I... don't really know how to explain.'

'You let me even when you don't want to? Why?'

Derek nodded. 'Because you want to.'

'That doesn't make me less worried about it.'

'I could say no, but I don't. Even when I don't really want to...if I let you, it still feels good. Calms me. Makes me feel better. I suppose...I suppose it's because I trust you. I trust you to know what I need better than I do. If I didn't, I would say no to you.'

'Oh.'

'That's weird. Isn't it.'

'Maybe. No. Not weird. Just different. Not bad. Do you...have you ever heard of free use?'

'No.'

'It's where you effectively consent to be used however and whenever I want.'

'Like your sex slave.'

'No. And yes. You could have a safeword. And if you prefer we can negotiate restrictions, limits, things I'm not allowed to do or...'

'No!' Derek all but yelled.

'Okay. It was just an idea,' Stiles said, sounding utterly dejected.

'No,' he said calmer. 'I mean no restrictions. I trust you to know when to stop.'

'You mean you want to do it? What about a safe word?'

'No. At least not for that. Maybe if it's something specific and you want to be extra sure we can have one for that, but no. From now on...' Derek took a deep breath. 'From now on you have permission to use me however you want, or however you think I need.'

'So, to be clear, I have your permission from this point onwards, that you can be used whenever I choose?'

'Yes.'

'Fuck yeah!' Stiles crowed, going so far as to punch the air. Derek had expected to get pounced. But all he got was a sweet kiss on the lips when Stiles left just after ten.

The next evening Derek was reading again when he heard a stuttered heartbeat and someone cursing as they struggled to slide the elevator doors closed. He smiled despite himself. Stiles. A few moments later, the sliding door opened and in he came, carrying a duffle bag which was dumped on the sofa next to Derek.

'Hey sour wolf,' Stiles said, before planting a peck on his lips and wandering off to the kitchen for one of the disgusting craft beers he insisted were kept in supply. 'Take off your clothes and kneel on the rug,' was yelled back to him.

Derek froze, realising this was it, what was agreed to last night. He wasn't in the mood, really would have preferred to cuddle up in silence each reading their own thing, just being together. But, Derek realised, doing that would have still been miserable. Quickly he did as he was told, stripping of the sweatpants and threadbare muscle shirt he'd thrown on after his shower not long before. There were no socks or underwear to worry about. There was electricity skipping over his skin as he knelt there, a weird buzz. It took him a while to realise that while he'd let Stiles top whenever he wanted and readily agreed to this free use thing, he'd never actually wilfully submitted. Not totally, not wholly, not to anyone; ever.

Stiles came back to sit on the couch next to his bag, only he'd not grabbed a beer. It was a Dr Pepper. After a couple of swigs just sat there playing on his 'phone, occasionally glancing at Derek, he opened the bag and began pulling things out. Some large black candles, a blindfold, nose clip, heavy-duty earplugs, and a good set of noise-cancelling earphones.

'So, given that you've given up your right to say no, most of this is unnecessary, but I think it'll be more fun for both of us if we use it. What do you think?'

Only a second to think about it, but a look down at his crotch and his hard dick staring back at him gave Derek the answer he needed. A nod. Something took Stiles took over then. He didn't look like Stiles any more. Instead, someone absolutely sure of his place, confident in his position and in his body and Derek felt utterly owned. It made his cock twitch. First came the blindfold. That wasn't as bad as he expected, smell and sound much more powerful for him as a werewolf. Losing the spicy scent of Stiles' arousal when the nose clip clamped his nostrils shut was harder. For one because the aromas filtering in through his mouth as he breathed were muted and confused. But also as he realised that if his mouth was fucked, as Stiles was sometimes wont to do, he'd have no backup air through his nose.

Finally, the plugs were set into his ears, and everything went quiet. He could barely hear anything outside of his body. There was still directionality, could tell where Stiles was when he unlocked his 'phone and sent a text, but he couldn't hear his heartbeat. The noise-cancelling headphones squeezed onto his ears, and all he could hear then was his own pulse pounding in his head. It was slow and steady, and it surprised him that it wasn't racing. Apparently, even his subconscious had complete and utter trust in Stiles. Music started then, assumedly to ensure he couldn't hear any external noise.

Then nothing. Whether a result of having his senses dulled or because a great deal of time had really passed, Derek wasn't sure. His time kneeling naked in the middle of the room, dick hard and throbbing in time with his heart, seemed interminable. He couldn't remember that last time he'd been this calm and relaxed without a nagging feeling of restlessness. A hiss escaped his lips as the first drop of burning wax fell on his strained thigh. Placing his hands on the floor behind him, he leaned back, presenting more flesh for the hot liquid to hit, exposing all of himself to the painful sensation.

A drop on a nipple drew a whine; the next hitting the head of his cock where the skin had pulled back made him roar. Again and again, the wax fell on him and burned his skin as it solidified. Each time he waited in anticipation, wondering what sound it would draw from him, even though inaudible to him. Like the initial waiting had seemed to go on forever, the same feeling occurred with the wax. It was surprising each time he shifted, and the dried wax pulled, that his body wasn't encased.

Eventually, it stopped. Naked skin, legs, pressed against the sides of his thighs, someone standing over him, and Stiles hard dick pressed against his lips. Derek opened up, and it slid in just slow enough to give him time to get used to breathing through his mouth while getting his mouth fucked. Then the pace picked up. Something seemed off about it the taste and texture, but he put it down taste devoid of scent. Eagerly he sucked and licked, opening up his throat as it sank in deep, over and over again. Sweet and salty and thicker than expected cum filled his mouth, devoid of the bitter aftertaste of massive coffee addiction.

Unbelievably soon he found himself pushed forward to rest on his arms. Fingers rubbed cold, slick liquid on his hole though they didn't press in. After they withdrew Stiles' cock started to slowly force its way past the initial resistance of his hole then sink inside. Confusion sparked in his mind when it bottomed out much deeper than it ever had before. It was easy to write it off as position and dulled senses, and it didn't stop him bearing down and pushing back to meet the thrusts. By the time the pace stuttered, and he felt hot cum spilling deep inside him, he'd dismissed any notion of wrongness. This was right, wholly and utterly.

Frigid air flowed inside him on a draught as the invading flesh withdrew, making him shiver and he was pulled back up into a kneel. First, he felt the cum begin to dribble out of his hole onto the backs of his heels, making him itch, then the press of a semi-hard dick against his lips. Surprised at first by the clean taste where he had expected to enthusiastically slobber on the taste of cum, lube, and his own ass, it quickly passed. Bobbing up and down, tongue flicking, he worked the cock to hardness and confusion returned. There was no question this time though that this was his place, confident in its rightness, even as he knew this was too thick, the wrong shape; it wasn't Stiles.

Then, pushed forward to allow access to his behind his head sank down into thick wiry hair. His throat constricted, struggled to open, unable to breathe through his mouth with this monster blocking the air's only passage. Slowly he was pulled back to sit of the cock now pressing into his hole. Supported by a chest that was thicker, more muscled, hairier than Stiles' they began to rock into each other. Then he remembered what was agreed to. Not that Stiles could use him whenever he wanted, but that he could be used whenever Stiles wanted. Not one of the cocks he'd taken had been Stiles.

Almost like Stiles was waiting for the realisation, reading his mind, the music stopped and the headphones removed. 

Vaguely he could hear conversations, laughter, bottles clinking, over the sounds his own slurping made. Next, the plugs were taken out, and the sound flooded back in. The droning noise he's heard was his own chest, purring around some anonymous cock. So many heartbeats pounded in his ears.

Blinking back the light as his eyes tried to adjust after so long in darkness, he peered up over black pubes. They lead to washboard abs, a muscular chest, to looking into his Alpha's eyes. Scott sank deeper into his throat with a grin as Liam whispered into his ear from his place behind. 'Your ass is the best thing I've ever stuck my dick in, Derek.'

What came next would either cement this as Derek's true evolution and reawakening or send him into a blind panic. Stiles had, either ingeniously or by terrible misstep, left scent until last. A hand, long slender and dotted with moles, moved Infront of Derek's eyes and pulled off the nose clip. The flood of olfactory sensation would have been too much. Should have sent him reeling and running to hide if one particular scent mixed into the soup hadn't grounded him. If the cock's sawing in and out of his holes hadn't reminded him of his new position.

Eleven men used him as they wanted through the night At some point worn out at ready to leave Stiles made his speech, waited to the end so Derek could here. Free use pack toy, wherever and whenever, as long as Stiles approved.


	8. Day 7 - Rimming | Breeding | Tentacles

**Summary for the Chapter:**

> Turns out they missed a chimaera and it’s got its sights on Theo. Luckily for Derek he’s there when it catches up to its prey.

**Notes for the Chapter:**

> RImming, Breeding, Tentacles, Cum, Knotting, Forced Sex
> 
> As tentacle monsters are wont to do, they fuck first and ask permission later (if at all). Despite all turning out fine in the end, this is definitely dubcon and for at least one participant possibly even noncon. Please be aware before reading.

They were being followed. Theo was acting cagey, and Derek was in no mood for games. Especially when it turned out they were being herded by a chimaera they didn't know about because Theo didn't fucking tell them. As they stopped in the mouth a cave to catch their breath, he got Derek's patented glare. The one that was usually reserved for Stiles.

'I swear,' panted Theo, 'that I didn't know. I just thought someone was watching me, or maybe that it was just a regular human weirdo. I thought all the chimaeras were accounted for.'

'You collected their fucking parts,' Derek groused. 'And now, we're going to get eaten because you can't fucking count.'

Theo opened his mouth to argue back when the crack of a branch sounded from a few feet away just outside the cave. Either of them had heard it approach. In fact, they looked at each other confused, they could only hear each other's heartbeats. A silent conversation on fight or flight passed between them, and they squared up to the entrance only to back up in shock as their pursuer stepped into the cave.

A human shape stalked towards them, and they kept backing up. Its face seemed to be slowly liquefying even though it kept its vague form. Maybe more worryingly it started to take its clothes off, leaving them facing off against a human-shaped jello. What happened next changed everything. Its arms began to shift into long tendrils, where its groin and nipples had been more appendages sprouted.

Further growths appeared from its chest and back until a writhing mass of gelatinous tentacles on legs stood before them. Theo's heartbeat began to speed up, and the smell of fear filled Derek's nose. His own reaction was different. And probably not typical. His own heartbeat had picked up from excitement.

Next to him, he felt Theo gasp and swing his head. Derek couldn't help himself. Cock hardening in the tight confines of his jeans, he was filling the cave with the scent of his arousal. It burned his own nose and filled him with shame at the thought of how disgusted Theo must be. What could he do, though? Backed into a corner by a real-life tentacle monster. It was everything from his dirtiest dreams come true.

One shimmering blue tube made its way over to Theo and started to move over his exposed skin, tasting him, leaving behind a thin, sticky film. Then it wrapped itself around his neck. 'You're unfuckingbelievable, Hale. We're about to get eaten by Cthulhu, and you're getting off on it!'

'I'm sorry,' Derek sobbed as another blobby arm began to inspect him. 'I can't help it. I've just always had this fantasy, and even though I'm probably going to get us killed apart from that, it's exactly this.'

'Including me? I knew you had to be into some perverted kinky shit, but I couldn't put my finger on what and now…' Theo trailed off with a gasp. The tentacle on Derek had stilled then the monster began to vibrate, changing colour. Now a deep pink a cloud of vapour started spreading from its flesh. It stank of concentrated arousal. Like sticking your nose in the crotch of someone who'd been leaking into their shorts for hours. 'Oh fuck, now I'm getting turned on.'

The hold against Theo's neck released, but before either man could move, they found their limbs all held tight, and their bodies lifted from the ground. More of the prehensile tubules began to tear open their clothes. Theo turned his head to glare at Derek. 'We're going to get fucked by this squid, and you love it, don't you?'

Derek wasn't able to answer. One tentacle had wrapped itself around his angry red cock, another was pushing into his throat. It seems he could still breathe, but the volume of the thing making its way inside him

was making his throat bulge obscenely. Theo had never seen someone's cock so hard, so turned on, that it looked painful. Begrudgingly his own cock started to swell up as he watched the scene before him. Until that point, beyond holding him out of the way, it seemed the creature had been ignoring him. Apparently, his arousal was all the consent needed for him to be brought into the action.

Suddenly Theo tipped back, and the next thing he saw was Derek's hairy ass lowering onto his face. For a moment he considered not playing along, then a pressure began to build up at his hole. A slick undulating tentacle began to push inside him, filling him further than anything he'd ever experienced. As the pressure built but no pain came, only more and more pleasure, his mouth opened and his tongue began to prove enthusiastically at Derek's hole.

It seemed to go on for hours. Eventually, Theo felt a warmth begin to spread inside him, and the tentacle started to withdraw. Behind it, pints of a thick liquid filled his guts. It was a surprise when he closed up, and it didn't all come pouring out. With no patience, the creature pulled him away from his feast of fat ass only for their positions to be reversed. Derek didn't hesitate, immediately latching on to lick and suck the thick, goopy syrup from Theo's well-used cunt. The moan into ass gave away when the tentacle pushed inside him.

The sensation of having one of the wriggling slimy limbs push inside his mouth and begin to force itself down his throat panicked Theo. At least until he was sure that oxygen was still getting to his lungs. How? He didn't want to think about. Like his ass before, his belly was eventually filled with warm fluid, almost to the point of over fullness. Sated it seemed, the creature turned its attention to their pleasure.

They were pressed face to face and, despite where they'd been, didn't stop to think or talk as their mouths met, tongues fighting, as they searched for the taste of each other.

What happened next was almost the best part for Theo. He was lined up and pushed inside Derek. They didn't have to do any work as he was fucked inside the tight hole like two toys being played with. Suddenly a smaller firmer jelly finger pushed inside him, and hard against his prostate and Theo howled as his cum filled Derek. Their places were switched, and the thick rock hard uncut cock made him whimper as it filled his over sensitive ass. It was still perfect when he felt the flood of heat inside him and the knot forming, locking them together.

When they woke up, it was light outside. Derek was still locked inside him but had shrunk enough he'd be able to pull out with only mild discomfort. They didn't see any rush to move. Head pillowed on Derek's muscled chest, hair tickling his chin, Theo mumbled, 'I might be a bit of a pervert too.' He'd have to make Derek laugh more.

The next month Derek turned up to their weekly pack get together with an equally hot man on his arm who he introduced as his new boyfriend, Trevor. It didn't really surprise anyone. What did was when Derek announced Theo was also their boyfriend, and it was a poly relationship. Not least for Theo himself though he managed not to give anything away. 'We met last month,' Derek said grinning. 'On a run through the woods.' Theo's dick was instantly onboard and sure the rest of him would follow.


	9. Day 8 - Casting Couch | Bukkake

**Summary for the Chapter:**

> Derek had his solo casting and is back for the group. All the boys jerking off into his face while he strokes himself off.

**Notes for the Chapter:**

> Casting Couch, Bukkake, Cumshots, Situational Humiliation (mild), Porn Acting, Sex on Camera.
> 
> Enjoy!

Somewhat nervous but quietly confident, Derek strode into the same nondescript office building he did the last time. Flashing his come fuck me grin at the receptionist, 'Derek Hale,' he said, waiting for the girl to stop blushing. 'I've got an appointment with CSM, the modelling agency.'

A few taps at the keyboard and he was sent off to the elevator with a key card. 'Third floor Mr Hale. That'll get you into their lobby, they have their own receptionist.'

'Thanks,' he replied, shooting her a wink and grinning broader as her blush spread.

Not long after the speaker pinged and the doors slid open and his ascent began. Terrified was how he felt the last time he was here; the first time he was here. Money was in short supply after they'd moved out to New York. The money was all Peter's, their half in trust until Laura turned thirty. She'd been furious when he'd told her about the job, but she got over it. Lost in thought the doors slid open without him noticing and left him darting out as they began to close. Last time he'd been on his own, just him in front of a camera, being made comfortable by Boyd who had been filming. This time they were trying him with some of the other models, seeing how he'd fit in.

With a swipe of the card over the NFC, the frosted glass doors slid apart, leading him into a small foyer. A couple of soft leather couches lined two of the walls, and he took a seat as the desk in the corner was empty.

'Derek,' a cheery voice rang out not long after he'd taken out his 'phone to distract from the silence and avoid making himself anxious. 'It is Derek, right?' A tall slim man with a mole dotted face held out his hand. 'I'm Stiles.'

Stiles was cute. Derek shook his hand. 'Yes.' Laura found it hilarious that he could charm the pants off of anyone, as long as he didn't want to. If he actually liked someone, he reverted to caveman grunts and scowls.

It didn't seem to put Stiles off. 'Great! We're a bit short-handed at the moment, so I'm doing three peoples jobs. Do you want to follow me and I'll go over the initials with you? Everyone else is all set so if you're ready we can start straight away.'

'Sure,' Derek replied and stood to follow, letting the sound of Stiles chatter wash over him as they went into what seemed to be an office cum ensuite with a shower.

'Okay dude, first of all, you did the solo last time, all went okay?' At Derek's nod, he continued, 'we got your test results through and your signed release. Any questions since last time?' A shake this time. 'Cool. Well, first things first, we're gonna want you in a suit, which isn't what you're wearing, and I'm sure you don't want cum all over your own clothes.' Stiles smirked as Derek blushed.

'No.'

'Thought not. Do you want a shower? There's no penetration for this one, but it's up to you.'

'I showered before I set off. I'll just start sweating if I get another.'

Stiles' eyes seemed to drift for a moment before snapping back. 'Not sure that's a bad thing dude, but sure! Anyway, wait, you did get told what's happening this session right?'

Derek nodded again, and at Stiles' dubious look managed to croak out, 'yes.' It didn't improve the look on Stiles' face. Still, he did bend over to pull out a bottle of water form a minifridge under the desk. At least Derek got to ogle the guy's ass before getting kicked out was the thought that flashed through his mind, swigging the liquid. And probably the reason he choked. 'Yes. Someone called Erica? Talked me through what would happen and what I'd need to do.'

'Great. She's filming slash directing today. Not a problem is it, having a woman in the room?'

'No.'

'Some guys get all uppity about it. I really don't get it. I mean it's a job, right?.

'Em,' Derek began but wasn't really sure if he was even meant to respond. Any reply was interrupted before it was formed.

'Anyway, I need to measure you for the suit. We want it very well-fitting, but you need to be able to kneel without it splitting. You want to strip or shall I do it while you're clothed? Either way works for me, but it's more accurate if you aren't wearing anything. And I promise no naughty touches,' Siles said with an angelic grin on his face.

Again Derek got as far as saying, 'err.'

Stiles' grin turned positively filthy and licking his lips he continued, 'of course in an hour I'm going to be cumming on your face, so there's no need to be shy on my account.' The man winked. Actually winked. And Derek had unbelted his pants and shucked his shirt before he even realised what he was doing. A burning spread over his face and down his chest as he felt himself blush. Stiles was, however, professional in action if not words, and quickly took Derek's measurements as he stood there in only trunks, before going to fetch the wardrobe items. Just before the fidgeting started, Stiles returned.

'Okay, dress socks and sock garters, check.' He handed them off to Derek, who sat on the corner of the desk and began to pull them on.

'I'm not actually getting naked, am I?' Derek asked as he clipped the odd devices to the tops of the socks. It startled Stiles out of his stare which had been directed at the now clothed feet.

'Err no. Why?' Derek snapped the elastic of the suspender he was currently attaching to the right-hand sock. 'Oh. Erica put them on the list. She's a stickler for realism, I suppose. Get's you into the character of a high flying executive who...,' at Derek's dubiously raised eyebrow the rambling explanation stopped. 'Dude, fucked if I know. I get what's on the list, you put it on. I'm paid to fuck and file. You want insight into the creative psyche? Ask someone else. I think Isaac might be writing a paper.'

'The viability of asteroid mining in capitalist society; Psyche, a case study,' Derek mumbled.

A confused response came alongside a black cotton long sleeve button up. 'Huh?'

'Isaac is writing a paper for his masters on the asteroid Psyche, not "the psyche".' The shirt was tight, but after a few testing twists and flexes, Derek was confident it wasn't going to split. The gaps at the buttons would probably pull apart a bit, show some skin of his haired chest.

'Oh. Then I don't know what to tell you, Dude, but you look good in sock garter's so I'd just roll with it. Wait, you know Isaac?' A skinny dark grey tie was handed over next, complete with a tie pin. Luckily Derek knew how to tie one.

'Yeah. We've been friends a couple of years. He's the one who referred me.'

'Oh,' Stiles sounded genuinely surprised. 'So do you two…, you know?'

'No.'

'It's not going to be a bit weird then? Today.'

'I hope not. We've talked about it. If we only do it here, when we're getting paid for it, why can't we keep it professional? Like you said, it's a job, right? Pants?'

Stiles looked confused at the non sequitur before realising he was still holding the rest of the clothes and Derek's legs were still bare. 'Oh. Right. Err, you're supposed to be...'

Derek grunted and stood up, peeling his trunks down and slipping them over his feet before standing back up straight with his hands on his hips. It was his turn to get the upper hand. 'Commando?' Stiles just nodded and proffered the trousers. These were a dark grey, more charcoal than the tie. They were slipped on quickly, and the final piece was handed over, a pair of well-polished oxfords.

'Very nice,' Stiles mused. 'Ready?'

Not wanting to put it off in case it resulted in cold feet and second-guessing, Derek nodded, then followed Stiles down the hall to the room next to the one he'd done his casting couch jerk off the last time. This was his next and final casting couch test. If this went well, he'd go on the agencies list of regulars. It wouldn't guarantee an income, but it would be better than the barely scraping by they were managing now. The room he was lead into was dressed up as a flashy modern office. The others who'd be joining in were already there waiting, as was Erica with the camera.

'Batman, about time. Introduce him to his new colleagues, and then we can get started. You all know what's what, I want to see whether he's a natural of if he needs a lot of direction.'

'Sure thing boss lady,' Stiles said with a sloppy salute before dragging Derek over to a trestle table loaded with fruit and juice and surrounded by a group of men.

The premise was simple enough. Derek wasn't expected to do any acting. If it worked, they'd film that bit later. Stiles would lead his fellow interns in a sexy revolt against their mean and incredibly fuckable boss. Isaac; Boyd, the cameraman who filmed Derek's first session; a puppyish guy called Scott. Finally, a sullen-looking guy named Liam. They would all bust into the office where Derek was working on the computer, then the fun would begin. When it was time to start, it seemed unnerving, just him, Erica, and a camera in the room. When that door burst open, and Stiles started to ad-lib, Derek couldn't help just falling into it. His naturally submissive side rising to the surface as he tempered it with the role he was playing.

'Harris,' Stiles yelled, making Derek's eyes shoot up in surprise. They'd agreed to use a fake name for this and decide whether a stage name or his real name was the preference for the long run. Stiles had seemed almost gleeful when Erica has agreed to his suggestion though.

A scowl slipping into place, Derek found it easy to fall into the scene. If Stiles was going to impart some drama he could too. 'What the hell are you doing, barging in here,' he growled out, standing. The chair rolled back and crashed into the window a few feet behind him, but no one reacted or called a stop. 'I can fire you, you know.'

'Adrian, Adrian, Adrian,' Stiles said with a tut. 'What are we going to do with you?'

'It's Mr Harris, to you... Interns. You shouldn't even be talking to me. It's why I have managers to...' his voice cut off with a click as Stiles had walked up to him, wrapped the silk tie around his fist and pulled Derek forward until their noses were nearly touching.

'Adrian.' A sultry sound than made Derek's dick twitch despite himself. 'From now on you're going to be calling us, Sir. Things are going to change around here, and we're going to make sure to take out benefits in kind as long as you think minimum is good enough.' Lead by the silk around his neck, Derek followed around the desk where he was pressed back to sit. Stiles moved forward and pressed his mouth to Derek's, licking and pushing with his tongue until lips opened and allowed entry. To stop himself toppling, Derek planted his hands on the desk, spread his legs to let Stiles closer, and moaned around the invader licking into his mouth.

After what felt like hours, Stiles pulled back, laughing as Derek started to follow with a whine, only a hand to his chest stopped him falling forward.

'Such a responsive slut, isn't he boys?' That was when Derek remembered the rest of the cast. His eyes shot up, and he was met with the sight of four smoking hot men stood in a semicircle, dress pants unzipped, and big cocks being slowly stroked. Derek licked his lips as he stared, and he was pulled to his feet. Stiles rubbed a hand over his crotch and chuckled when the hard dick he found twitched in his palm. 'Such a slut, dude. Get on your knees.'

Derek dropped and held back a wince as his over-eagerness was too hard on his knees. Stiles stepped back, and the other four moved forward. Unless he was told to, Derek decided that the situation called for him to leave off his own hardness as they began to speed up their stokes inches away. His hands wanted to move, his left started to rub at his thigh, the right moved up to his chest and began to rub and massage his pecs as his stared entranced at hands striping over hot flesh.

'Such a needy slut when you get down on your knees, eh Harris?' The derision sounded genuine, and it just made Derek harder, twitching in his pants he felt wetness leaking from his tip. 'Fuck, Harris you're leaking through your pants, look and that damp patch. Take your cock out, let's see how hard you are for us.'

As instructed, Derek unzipped and tried to fish himself out. Stuck in the tightness of the pants he had to rise up on his knees bringing himself with inches of the stroking dicks. As he began to settle, open to the air, his hand pulled back the skin covering his mushroom head, and precum poured down his shaft, soaking into the crotch of the pants. 'Well fuck, would you look at that? Boss man's a slut, no underwear for easy access. All hard and dripping from his interns using him. Don't touch that little dick now, keep playing with your titties, Adrian.'

Another spurt of precum leaked out as the words washed over Derek and he began to squeeze the muscle and pinch at pebbled nipples. A groan made him look up. Isaac's eyes were closed, mouth open, and a second later cum began to shoot from his long thin cock. The first shot hit Derek's chin, one drop on his lip. Next two spurts landed on his neck as his head tilted back, and the last few stained his silk tie and shirt as he rubbed the mess into his chest. Isaac tucked himself away and turned without a word, leaving the office, closing the door softly being him.

When Derek licked the single drop of cum on his lip it proved too much for Scott who roared as he began to spray. These weren't neat streaks but seemed to spritz in all directions. If this had been real, where it would have been easy enough to discard the tie and hide the mess from Isaac under a vest or buttoned suit jacket; Scott demolished his shirt. From where it was tucked into his pants to the perfectly pressed collar, Derek was splattered with a mist of tiny drops of semen. Scott patted Derek's head and trotted out of the room, not bothering to tuck himself away.

Boyd was next, all business and perfunctory. And the biggest of the bunch. Derek very much wanted to choke on Boyd's cock and swallow his load. Now, it was directed down, and his spend soaked into the grey pants and coated Derek's own cock. A small nod was all the acknowledgement he gave before tucking up and leaving.

Next came the piece that Derek had most wanted to try getting fucked by. Like himself, Liam was uncut and a profuse leaker, but he also sported a thick steel ball closure ring hanging from his slit. Derek was sure it would feel like heavenly torture pounding into his prostate. For now, as had been agreed, Liam pulled forward Derek's head and began to spill into his hair. It was a bit disappointing from his perspective, not being able to see or feel it, but it probably looked good on camera. When he tilted his head back, a large drop of cum hung from the piercing at the end of the softening cock. Liam scraped it off and sucked it into his own mouth with a wink, then like the others left the room.

Only Stiles remained. Slowly he wandered over, smirking. 'You're a mess, dude.' Stroking himself, he began to undo his pants, then stopped when Derek whimpered and licked his lips. 'Maybe you should do the work? What do you think?' It wasn't part of the plan and was said quiet enough it could easily be edited out, but Derek wasn't going to pass up the chance. Hands shaking slightly, he began to open Stiles fly and then pulled out the most giant dick he'd ever seen in his life. Where Boyd's had been significant but proportional, Stiles' was a monster. The day it destroyed him couldn't come soon enough, but for now, he began to stroke. It quickly became apparent this was a two-hand job and picked up his speed as both wrapped around the shaft. This wasn't going to take long, Stiles had been keeping himself close to the edge while he waited for the others to finish.

'Gonna cum. Shoot my huge load all over your cum slut face,' Stiles choked out. Then he did. Barely time to close his eyes and, regretfully, his mouth, Derek felt powerful shots of thick liquid hit his forehead, nose, cheeks and chin. The last two blasts were directly against his lips and didn't help him in keeping his lips pressed together.

When he opened his eyes, Stiles was grinning down and him. The last drops were being squeezed onto Derek's ruined clothes, and he carefully tucked the now shrinking cock away. 'Good boy,' Stiles said. Boot pressing into the bottom of Derek's balls he snickered, 'I'm sure you can deal with that yourself.' Without bothering to wait for an answer, he made to leave.

Derek nodded, and as the door opened, he called out, 'oh, and Stiles?' The man turned back with a raised eyebrow. 'Don't call me "Dude".' On a laugh, the door closed and Derek grabbed on and slowly began to stroke. 

Contrary to everything he's ever learned about acting, but what he'd been told was expected at this point, he looked directly into the camera. He began to speed up the movement of his hand over his ready to blow meat. Relinquishing his tortured nipple, he brought his hand to his face and swiped a sizeable dollop of Stiles cum onto his fingers. Cumming hard with a groan, he sucked the sticky goodness into his mouth.

'Well, fuck. Erica said. I think you're hired. Welcome to Cum Soaked Men. You truly embody our ethos.'


	10. Day 9 - Pegging | Emetophilia | Clone sex/Selfcest

**Summary for the Chapter:**

> Stiles wants to get brutally skull fucked 'till he tosses his cookies. It's a lifelong dream. Unfortunately it's difficult to find a willing partner for that so he made one. Why not a copy of him self.

**Notes for the Chapter:**

> Pegging (male construct), Emetophilia (puke), Clone sex, Selfcest, Throat fucking, Messy Sex
> 
> Warning: contains puke play. If vomit's not for you, skip this chapter. Also contains the suggestion of noncon voyeur joining in uninvited.

Stiles had always loved it when he puked but never made himself sick on purpose. As enjoyable the idea of shoving something down his throat was, once he began to associate the sensation with arousal he didn't want to make a habit of it. And when he started having sex, there weren't many people willing to indulge that particular kink. The chimaeras were what prompted him to wonder.

As was typical for him, research was the name of the game. It took months of trial and error. Now, he can conjure up a simulacrum or at least an acceptable copy. It doesn't have distinct fingers or toes, and no matter what he's tried, it's always void of genitals. Still, add a strap on dildo, and it will pump its hips until Stiles is so worn out his will can't hold it in place anymore. There's a bit of a mess at that point as they kind of…melt. After the first one, the lesson was learned. It's the bath or in a paddling pool on the floor of his room. It was a flaw that he was still trying to iron out.

The dildo he'd bought online had been thoroughly tested the last few attempts. Strap in on to the clone, order them to their knees, get on all fours, back up, and say the magic word. If he ever got a girlfriend, she better be into pegging because he wasn't giving this up. The rubber cock stretching his hole and relentlessly battering his prostate was the last test before he knocked it up a notched. The next time he'd indulge his literally sickest fantasy. The thought had him cumming untouched onto the bottom of the tub. Seconds later he was showered in thick gunge, and the now unsupported cock slipped from his tired hole. Tiredly he started up the shower. It was a good job he'd worn himself out, or he'd be too wired. The anticipation of the next day's attempt was beginning to build.

Despite the added danger of mess, the decision was made to proceed with the evening's activities in the blow-up pool. It had the advantage of being able to warm up with some of Stiles' favourite porn on a screen big enough to see it while he lazily worked the foot pump. Once sure that alone time would remain alone time, he stripped off and got in the pool, strap on by his side, and began the summoning. Ten minutes later, a mindless copy of himself stood waiting for instructions. It was like a charcoal sketch that someone had swiped their thumb over, losing some of its defining features. While it still lacked a cock, the mouth hole was more formed than the previous fully fused or stitched together versions, and Stiles could envision a future of putting it to use.

For now, there was another plan. Attaching the harness and dildo to the golem, knelt and prepared himself. Readied himself really, the preparation had all been done long before. In an emergency, a specific thought would melt the clone construct, and his belly was full to bursting moth soft foods and milk.

Slowly Stiles began to bob his head up and down the silicone shaft, just too thick to be comfortable. With a flash of a visual, pictured in his mind, the oddly pale, almost translucent, and webbed hands of the copy moved to hold his head in a firm grip. Then the thrusts began, slow, steady, not too deep. Relaxing his jaw and stress dying his breathing, Stiles ordered the copy to push in all the way. The dildo stretched his throat and tickled at his gag reflex, but he held back, for now, taking in air through his nose and pressing his nose into the soft belly of his living toy.

It was only seconds, but Stiles felt like he was flying for hours, then the thought crossed his mind, and his dreams came true. Move. No delay, no caring for his well being, no checking in, the golem pulled out until the head of the fake cock hit the back of Stiles' teeth, followed by a cough. The splutter cut off as the invader sank back into the depths of his throat, and he began to choke.

Already rock hard, Stiles started pumping his prick, no lube needed as thick slimy spit was pouring from his mouth on each reverse thrust. Less than a minute in he came, splattering his chest and the bottom of his chin, but he kept fisting his sensitive cock. It didn't start to go soft, the edge was barely taken off. Regardless there would be no stopping until he got what he needed.

The bile rose suddenly and unexpectedly, forcing out around the blockage pushing back inside. As it sprayed over the golem's crotch and dripped noisily to the plastic pool base, Stiles began to choke and splutter. That was the tipping point. Puke, in earnest, began to bubble up, pouring from his mouth, falling onto his body and coating his cock. It was thicker and less smooth than he had expected, but it just made him hotter. More and more seemed to force its way up with each retch. His nose burnt and ribs hurt, but he kept taking the skull fucking until he was dry heaving and no more vomit remained.

Grabbing at the base of the dildo, with a thought the clone melted into thick slime. Throat full Stiles began to roll around in the combined mess and inch deep in the pool l, squirming and scooping it on to his body, coating his cock with it as he strolled harder and faster.

This time he came even harder than the last, the best and most drawn-out orgasm of his life. Slowly he pulled the dildo from his abused throat and dropped in in the puddle. Laying there panting, contemplating the cleanup and when he was going to be recovered enough to do this again, he missed the movement at his window. A thick cock, bigger than the dildo, rubbed against the glass. He didn't hear the sound of the window start to slide open, or booted feet hit the carpet.


	11. Day 10 - Daddy Kink | Somnophilia

**Summary for the Chapter:**

> Obsessed after a date, Derek sneaks into his older boyfriend's house to find them sleeping with their husband. Not to mention another surprise along the way. Peel off the sheets, crawl up their body and suck down their dick. Can't help themselves and get lost in it until hips start pumping into them and hands grab their heads. That's it, suck daddy's cock.

**Notes for the Chapter:**

> Daddy Kink, Somnophilia (dubcon), Face Fucking, Blow Jobs, Little Dicks, Implied Chastity.
> 
> Warning: dub/noncon somnophilia. It's implied consent is not sought before hand though everyone ends up happy with the situation.
> 
> Adults who're into older men and have a raging daddy kink.

They'd been on a couple of dates, discussed some of their kinks and Derek had been obsessed since Chris starting humiliating him in public. It was little things, calling him son, overriding his menu choices with better ones. It made Derek so unbelievably hard. Whenever they were out, he had to carry his jacket around in front of him. Chris had whipped that away on one occasion too, exposing Derek's obscene bulge in his too-tight jeans to the town's Sheriff no less.

Now he was trying the windows of the house Chris' SUV was parked outside of. Eventually, one slid open, and he climbed inside, only to come face to face with a blonde man sneaking in through the front door across the hall. They stared at each other for a moment, sure they'd each been caught, but something in their eyes told them they were in this together.

Slowly and quietly, they began to creep up the stairs. As they inched towards the master bedroom, their hands clasped together in a show of solidarity. Probably because both of them sounded like they were about to hyperventilate.

The door swung open silently, and Derek let out a gasp, the other man a whimper. In bed, asleep with his Chris was the Sherrif.

The other man bleated a sad, 'Noah!'

Derek was going to show Chris that nothing could be better than his skilled mouth, his need to please. He didn't care what happened next and slowly pulled the comforter from the sleeping men. 'What's your name?' He whispered to the other man.

'Jordan.' The reply sounded sad, dejected.

'Jordan, I'm going to crawl up that bed and show Chris that I'm the boy for him, and I think you should do the same for the Sherrif, show him how much he needs your mouth on his cock.'

'They're sleeping. I…maybe we shouldn't be here. We shouldn't be here.'

Like he'd not been interrupted, Derek just carried on. 'Do a good enough job, and maybe we can be brothers. Would you like that? Imagine us making out while our Daddies pound our tight holes.' Jordan seemed to be in a trace, so Derek started to strip off his own clothes then assisted the other. A buff body came into view, athletic, muscled, with a perfect round ass; just what oversexed daddies wanted. Like Derek, Jordan was rock hard and far enough below average to look small against his well-built frame. Jordan was cut though, which made him seem even smaller than Derek.

A little push and some encouragement had Jordan slowly crawling up the bed. 'That's it, little bro,' Derek said, making his own way towards Chris' thick flaccid cock where it lay against his thigh. 'Suck your Daddy down, make him fill your mouth and wake in pleasure when he cums. Let him know he needs you.'

'Daddy,' Jordan whispered before licking over the Sheriff's balls and sucking the cock into his mouth.

His own daddy to work on, Derek turned his attention back to Chris. Slowly he lifted the penis he wanted to ruin him and began to suck on the head. Had Chris been awake, Derek would have been upset by how long it took for his expert mouth to bring him to hardness. Years spent pleasuring older men made Derek, in his opinion, and expert. Not long after, tongue flicking and throat squeezing, he was filled with thick hard flesh and began to Bob, hand holding his prize in position. The minutes passed as he lost himself in his task, forgetting his surroundings.

Reality came crashing back down when the bed started to shake, and the sounds of spluttering and choking started from beside him. 'You filthy little slut,' the Sheriff roared, hands fisted in Jordan's hair and hips pumping hard, cock bashing into the unprepared throat. 'Breaking into my house, so desperate to suck on Daddy's cock? Well, now I'll make you take it.' Somehow the pace quickened, and Derek reached his hand out to grasp Jordan's, both a show of support and an act of congratulations.

A throbbing in his own mouth had Derek's eyes snapping up, over the plane of Chris' hard body to dark eyes staring back. Chris didn't do any work, didn't grab or thrust, just lay there watching as Derek continued to nurse at his cock. Then he started to talk. 'You're a naughty boy, aren't you, Derek? Sneaking into Daddies room. And I know you talked your brother into it. Look how he's getting punished, having his throat fucked to pieces. You know why I'm not doing that to you son?'

Derek's dick twitched in midair at the familial address. Slowly without stopping his sucking, he shook his head. He could guess, but Daddy knew best, and he would wait to be told.

'Because you want it. But you've been a bad boy, and you're going to be punished.' Derek sped up his bobbing, adding more suction to the vacuum in his mouth. Each time he drew back, flicking his tongue faster on the underside of Daddy's crown. Chris sighed, 'after tonight you're moving into the same room as your brother. And, while he gets to play all he wants, you're going to have your little toy locked away. And we'll only let it out if you're really really good.'

Untouched and undone Derek came hard, hitting his belly and dripping onto the sheets as his hips bucked. What knocked him over the edge he wasn't sure. Their adoption into the household or the promise of his little cock being locked up, both were enough to make him sob around Daddy's shaft.

Soon after Chris came down his throat with a moan, followed quickly with a bellow from the Sheriff and choking from Jordan. As they moved together halfway down the bed and shared the taste of their rewards with each, their daddies hands in their hair, they began to drift off. 'Welcome to the family boys,' the Sheriff mumbled sleepily. 'We're going to be very happy with you here.'


	12. Day 11 - Watersports | Temperature Play | Stockings

**Summary for the Chapter:**

> Stiles in his stockings and suspenders, lace panties and corset, ice cubes and hot water sucking Derek and playing with his nipples until Derek lets go, staining Stiles lingerie yellow, then Derek sucks the liquid out of his panties as Stiles pisses then pulls the panties under Stiles balls and sucks him off.

**Notes for the Chapter:**

> Watersports, Temperature Play, Stockings, Crossdressing, Corsets, Piss, Tiny Dick, Sucking, Fucking, etc.
> 
> No specific warnings here unless you really don't lace. Or piss.

Stiles always made a show of it, waltzing over to the bed, naked, pink and steaming from his shower. An inspection then, checking each item met his exacting standards and swapping out anything that didn't. Derek would just watch, cracking open a new beer each time the bottom of a bottle was reached. Sometimes Stiles took minutes, on one occasion, this ritual lasted for two hours.

First, without fail, the silk stockings went on, gossamer fine and pure white were slowly rolled up his legs. While not as hirsute as him, the slide of the silk over Stiles darkly haired calves never ceased to make Derek hard, building his anticipation.

Next came the lace panties, barely able to contain the package bulging at the front and perfectly hugging the fine ass stuffed into the back. Quickly a garter belt followed, keeping the stockings in place and sitting flat around Stiles' waist.

Now Derek was allowed to join in. Had to really as Stiles wrapped the corset around his middle. With reverence, Derek began to lace it up. Each time he pulled, a gasp followed, and he was almost drooling as Stiles' waist was cinched tighter and tighter. The garment's primary purpose was to squeeze an overfilled bladder. Still, they both enjoyed the aesthetic caused by Derek's ability to tighten it to Stiles' limit. Spinning around, Stiles showed off his now constricted figure. Rubbing at the bunched up flesh of his pecs, puffy nipples now stuck out in an invitation to be sucked. For now, Derek restrained himself. Dropping to his knees, he waited as he was passed one of the white stilettos. Opening it, he then rested the pointed ball against his belly and the tiny heel against his balls. A groan of sublime agony released when Stiles lifted his foot and slid it in, more force than was really required and a smirk on his lips. They repeated the process with the other foot then Stiles moved about the room as Derek went to fetch the rest of their equipment.

Quickly returning, he stripped down and sat in the chair in the middle of an empty stop of the concrete floor. Already his cock was hard and leaking in eager anticipation of the events to come. Groaning as he squatted down in front of the chair, Stiles was a sight in his lingerie, and with a tightly cinched waist, chest pushed up. He couldn't bend. And kneeling on the rough barely polished concrete floor would have instantly shredded the tights and quickly cut into his knees. That was a game for a different night. Now, squatted down, a picture of divine flexibility, Stiles balanced on the tiny points of his heels. With his back straight, he began to run his hands lightly over Derek's thighs. The plan had been perfected now after so many attempts and although somewhat predictable was never dull.

Somewhere Stiles had found and procured some clear bags with elastic ties at their openings; not large, just big enough to contain Derek's bull balls and a reasonable quantity of ever so slightly too hot water. Sack slipped inside and tied on, Derek released a hiss akin to one given when sitting down in the bath too quickly. This, they'd found, was the key to the crux of the evening. It had to be a wet heat to produce the right kind of relaxation.

The clink of ice cubes followed, Stiles' slender fingers rubbing the melting cubes first over his own puffy nipples firming them up, then over Derek's. Unable to help himself, although he was meant to keep his hands around the chair legs, Derek pinched hard at the now peaked nubs squashed up above the corset. The sting making Stiles moan and roll his eyes back.

A frozen had closed around Derek's shaft forcing a hissed gasp out of him and sending his hands back where they belonged. 'Naughty,' Stiles purred. Searing heat surrounded the head of Derek's cock and began to dribble down as Stiles' mouth, full of hot water, closed over him and started a slow shallow bob. The pattern continued, heat and cold, his nipples and his cock, driving him insane until he felt the snap maintaining his control. For a moment, Stiles didn't pull back, just swallowed around him.

Before it became a concern, Stiles pulled off and the fountain of golden liquid sprayed up into the air. Quickly he began to direct the stream, making sure it soaked his hair, covered his face, and began to seep into the white materials.

Pissing over his squatting boyfriend, Derek drenched the cotton corset, lace panties, and silk stockings and garter. The material began to show skin as it wettened, even as it turned yellow, staining the delicate fabric. It always fascinated Derek, as the steel ribs of the restricting garment began to stand out against the dripping wet yellow cotton. As his stream began to peter out, he took the opportunity to rub his stinking waste into his own skin matting down the dark hair on his belly and chest. Licking the last few drops from Derek's slit, Stiles removed the bag of now warm water from heavy hanging full balls and stood.

It was beautiful. The urine sodden lace barely contained the precious petit package as it strained to burst out of the material. Leaning forward, Derek began to lick and suck, tasting his own piss melded with the precum that had been slowly soaking into the crotch. Pressing down on Stiles' belly which was already squeezed tight by the corset was too much for his desperate bladder and his own stream released. Anxious not to let anything go to waste, Derek pulled him closer and sucked on the liquid bubbling out. Hands clamped around the back of Stiles' thighs, lifted him without breaking contact.

Legs wrapped around Derek's neck, weight supported by strong shoulders, Stiles bucked into the strong suction over his aching crotch. Every drop spilling from him was captured, savoured, and swallowed. Once the flow began to die down, Derek hooked a finger into the panty elastic and pulled it down to catch under Stiles' balls. Beyond the single admonishment, the first words were spoken since Stiles had gone for his shower. Tongue flicking out to swipe over steely flesh as his hair was coated in the last of the piss, Derek moaned. 'Mine.' Bucking twice Stiles pumped into the stubbled jaw, squealing at the prickling on his sensitive skin. 'Pretty little cocklet, all hard for me, stinking of our piss, so ready to explode. You're tiny little balls so swollen with cum for me to taste.'

As he was swallowed to the root, Stiles screamed and began to pump his hips, pressing the heels of his stilettos painfully into the muscle of Derek's back to gain leverage. His head was rubbing into the roof of the mouth so hot and wet around him. Never was his little dick going to make Derek choke and splutter but it all fit inside, and like every time, tongue slid out to lick under his tight ball sack and coax it to join the rest. Stiles knew when he'd cum, the swiping of a tongue over his most sensitive places and too much suction tugging his ball sack kept him on edge but never enough to tip him over. When Derek was ready two things, a combined over sensation that broke his mind would have Stiles shaking and squealing like a pig.

The back of the lace panties shifted over the hairy ass cheek helpless against the strength of Derek's fingers until the crack was exposed from one side. Slowly he began to rub and press, teasing the tight furl of muscle, damp with the mess of their earlier fun. There was friction on the outside, just enough for mild discomfort. But, as he pushed harder slipping inside, the resistance gave way to a slick, smooth slide, he had come to expect from Stiles excellent preparation. In no time three thick fingers had pushed in to the root and were curled applying pressure to the prostate. With a smirk knowing Stiles was on a knife-edge Derek bit down around his little mouthful and was rewarded with a flood of bitter saltiness.

What happened next was always a surprise for Stiles, Derek's time. Today there was no swallowing. Derek pushed his burden away far enough to spit the cum over his own cock and worked it in. Without warning, Stiles was span around, his back to Derek's chest, and slowly lowered down. As the tip of Derek's cum slicked dick kissed his hole his next was attacked with bites and suction marking him up while slowly sinking down until filled. There was no hard and fast fucking. Derek simply rolled his hips slowly, bruised up the pale mole dotted neck, and caressed the squashed cheats with once again puffy and sensitive nipples. Occasionally one had would slip into the wet repositioned crotch of the panties, flicking over the head of the now shrunken and sore little cock, circling like rubbing at a clit. Each time Stiles whimpered and cried, the rubbing stopped, only to resume when he began to moan in pleasure from the grinding fullness once more.

They stayed like that for hours, rocking to completion, exhausted, sated, and stinking.


	13. Day 12 - Feet | Shotgunning (fist & reach around) | Dacryphilia

**Summary for the Chapter:**

> Theo and Derek are left sobbing by Liam's dirty feet and Stiles' skilful hands.

**Notes for the Chapter:**

> Feet, Shotgunning (fist & reach around), Dacryphilia, Crying, Bondage, Sexual Neglect, Implied Orgasm Denial.
> 
> I've found various descriptions of what shotgunning is, but I'm a traditionalist (on this occasion because it's convenient for me). Shotgunning = the top fisting and performing a reach around, like pumping a pump action shotgun.
> 
> This is probably the shortest of these and I expect it to retain that title up to day 31. More of an expanded outline to porn or as I like to call it a sexy scene snippet.

It was always the same; in whatever way they rearranged, they all had their particular set pieces. Liam would grind his stinky feet into Theo’s face. His cock throbbing and leaking when a sob pushed air between his toes or fresh tears mixed with his sneaker sweat. Rarely would more than his shoes and socks be removed, usually content to let his dick poke from his fly. More than once, his pants proudly sported the fruits of his activities as he went about town. Liam would rub over wet cheeks, gathering up the salty liquid with lightly haired digits and then force his toes into Theo’s eager mouth. As much as it seemed to upset him being degraded and humiliated, Theo was always rock hard as he cried.

At the other end long slender and unbelievably skilled fingers attached to surprisingly large hands, slowly opened up Theo’s hole before sinking deeper. Stiles was addicted to the feel of tight muscle squeezing around his wrist as the thickness of his palm finally pushed through the resistance.

They’d tease the submissive playthings for hours. It was the same always, revelling in tears they made them spill. It there was one thing Stiles and Liam could agree on, they could both get off just from watching someone cry. Helpfully that also explained the muffled sobs and whimpers coming from the corset of the room. The reminder that sometimes Theo could be the one tied up gagged and untouched made him glad to take a whiff of foul foot odour and press back into the arm rearranging his insides. Sometimes he was the one tied up, sobbing and desperate, as Derek would be the one getting used.

As Theo looked over at Derek’s red-ringed eyes stained with moisture, the rock hard ringed cock, he’s glad he didn’t have to decide. A hand reached underneath him, Stiles, looking to tease, shotgunning him with no end to the edge and never over it. The fist inside him picked up speed, forming a ball and punching in and out. The toes he was sucking painted now in cum, along with most of his face.

Perhaps the only time it’s better if when Liam and Stiles fuck, slow and tender, the love between them evident, while Derek and Theo both sit in the corner and sob with neglect.


	14. Day 13 - Body Worship | Spanking | Frottage

**Summary for the Chapter:**

> Stiles is worshipping Derek, every inch of skin, every muscle, can't help himself from breaking the rules. Gets laid over Derek's knee and spanked until he's crying and fucking himself onto the thick muscle of Derek's hairy thigh.

**Notes for the Chapter:**

> Body Worship, Spanking, Frottage, Bruising, Rimming, Subspace, Cruelty, Implied CBT

Stiles knew the rules, and he broke the rules. For over an hour he'd been licking and sucking, kissing and biting, worshipping every inch of Derek's glorious muscled physique. For fifteen minutes he'd been struggling to breathe. Hairy thighs crushed his head as his tongue probed and prodded his favourite ring of Derek's muscle until his mouth was numb.

In a haze of sexual ecstasy, it was too tempting to suck a big bull ball into the warmth of his mouth. Ordinarily, it was appreciated, he knew. 'Stiles,' came the growled warning. Tonight was for muscle worship, nothing more. When he was ready, Derek would jerk himself off over Stiles and send him on his way desperate and untouched.

The ball dropped, and Stiles hung his head shamefaced. If he'd only moved on to what he saw below. Instead, his gaze went up, thinking of laving the now dried abs with a new coating of saliva. That's when the bead of precum, a single drop glinting like a precious jewel, caught his eye. Tunnel vision took over rational thought, and darting out his tongue, captured the drip of nectar.

Pain followed and screaming. Suddenly, without further warning, Stiles lifted from the floor dragged by the hair across the room to the couch. Lain over Derek's knee, sobs of sorry, sorry passed his lips. They were ignored. It wasn't better here to ask permission or seek forgiveness. Neither was ever given.

'Stop!' Stiles screamed, hoarse by the end of his first cry as Derek's palm fell on the crease of his left cheek and thigh. 'Please, I'm sorry I'll be good.' A second, third, and fourth strike fell in quick succession, near but never over each other. Half of his ass was already on fire, the untouched side felt frozen. It wouldn't last.

By ten, there was a puddle of tears, snot, and drool on the flow under Stiles' head. Another pool grew at the back end underneath the point his cock rubbed into Derek's thigh. He would cum here, like this, humiliated and sore, getting off to his punishment. The question was whether it would hold out until there were five strokes left or fifty. The number was never given, and Stiles suspected there wasn't one set. More likely, Derek picked a number to rein down after Stiles shot off against his leg, depending on how severe a punishment his anger warranted. It wasn't his place to ask, just to take and do.

Werewolf strength and healing meant Derek never had to worry about his own hand tiring and the bruises would remind Stiles of his place for days, if not weeks. By twenty, that part of his mind that so rarely let him in opened up, removing all distraction. Stiles began to moan, revelling in the burning agony. His hips bucked harder, seeking friction.

Twenty-one. His balls began to tighten.

Twenty-two. His ass began to clench.

Twenty three. With an evil laugh, the tips of Derek's fingers caught Stiles balls. Cum shot out at such force it hurt, soaking the underside of Derek's leg, firing drops beyond the pool of drool. Some even hit Stiles' chin where it hung over the edge of the other tree trunk thick limb.

In total, forty-eight blows had connected, though Stiles had stopped counting after he came; stopped screaming soon after. The rest fell as he floated in a trance. Dumped to the floor, in his own mess, sleep quickly overtook him.

Upon waking hours later, the sound of the weight machine being used set him crawling. Derek's naked, sweaty body was bulging with muscle and Stiles existed to worship. His eyes zeroed in on the stiff shaft of thick cock and he licked his lips.


	15. Day 14 - NTR/Cheating | Face-sitting | Collaring

**Summary for the Chapter:**

> Two assholes being assholes and Stiles being blissfully oblivious. For now. Cheating for the sake of messing with the person being cheated on more than anything else. In case it's still not clear here, Derek is a complete asshole in this but Theo is despicable.

**Notes for the Chapter:**

> NTR, Netorare, Cheating, Face-sitting, Collaring, Home Wrecking, Fucking, Breeding, Rimming

This was the first time the key had been used. Derek had given it to Theo with shaking fingers over three months ago but using it straight away would have been too easy. Making Derek wait, making it unexpected, strengthened the hold Theo had on him. As expected, the key worked and slipping silently inside was pleased to see the cables where the alarm unit had once been attached.

Theo jerked off under his desk in the middle of the office when Derek called him to bitch about that. Derek worried about it going off while Theo snuck in, reaching for arguments for why they should get rid of it. The counter-argument of a dad as a Sheriff really held more weight, so in a fit of pique, Derek had ripped the unit from the wall. It was when he'd said Stiles had started crying. Theo shot all over the carpet tile, getting odd looks from Sandra in the opposite cubicle.

Now it made him happy for another reason. There was no chance of him messing up and setting it off. Clicking the door closed behind him, Theo set off to explore the dark house. In the lounge there were framed photos of the happy couple; his favourite was the wedding picture. Derek had told him it had been Stiles favourite and now, looking at in Theo began to firm up in his jeans. A candid shot, he stood next to one of the grooms, taking his place as the best man, grinning at the camera. Stiles was leaning against him, gazing longingly as his new husband, Derek. Derek, who was being lifted up by Boyd and Isaac, his groomsmen, the line of his gaze bypassed Stiles by at least six inches to fall on Theo's face.

Moving on to the kitchen, there were Danishes laid out on the counter under a clear plastic cover. A single apple crumb Danish sat in the middle. Peckish, Theo plucked it out and began to nibble, spilling crumbs as he began to rummage aimlessly through the drawers. The lid, he left off, letting the rest to go stale. Apple crumb was Stiles' favourite, and Derek always left first in the morning. Assuming they didn't get caught beforehand, that would probably create an epic bitching out; maybe he could get Derek to record it.

Bored, the stairs were the next obvious choice. A cum stained thong was tossed into the basket on the floor of the laundry room in passing. An afterthought really, the plan had been to leave them under Stiles' pillow if the opportunity arose. The plush carpeting muffled any sounds as he crept up the ostentatious curved staircase. It was all Stiles. Derek was practical. This was proved when Theo reached to top and turned to face the master bedroom. Naked, kneeling, holding out a leather collar and looking incredibly guilty, Derek waited. It made Theo wonder, did the man do this every night? Waiting in pathetic, hopeful anticipation?

Taking the collar and strapping it around Derek's neck flipped a switch inside him. The guilt instantly melted off his face, and a desperate hunger took over. Now he belonged to Theo, Stiles be damned. Slipping past without a word, Theo began to shed his clothes across the floor. Naked, he sat back against the end of the bed, nearest Stiles' feet, and ordered, 'sit!' His head tipped back, waiting to be obeyed.

Rushing over, Derek turned, pulled open his fat hairy ass cheeks with his hands, and sank down to take his seat on Theo's mouth. The bent forward half-squat can't have been comfortable. Theo's hands could feel quads shaking as he moved them to pull Derek further down, making the position even harder to maintain. Not once did too much weight bear down. Stoically Derek hovered, hole applying just enough pressure to Theo's lips that he didn't have to chase it. Rimming an ass like Derek's was one of his favourite past times. Losing himself in the taste of sloppy hole was easy as he let the soundtrack of rhythmic snoring coming from behind them wash over him.

Once his tongue began to ache, and boredom set in a push to Derek's rump gave him room to rise up. 'On the bed,' he said, not bothering to whisper. Derek didn't seem to care, just moved as instructed. 'Hands and knees, push that pussy out over the edge, that's it. Stiles still make you wear condoms when you fuck him?'

A nod wasn't good enough, and the slap to Derek's ass sounded deafening in the otherwise quiet room; save for Stiles' obnoxious snores. A moan followed, 'yes.'

Theo snorted. 'Lots of lube, make sure you stretch, always douche at least an hour before,' he said snidely, a poor impression of the goody two-timed two shoes. 'I'm going to fuck you raw Derek, while your cuck of a husband is asleep next to you; just my spit and precum as lube. That's what you want, isn't it whore?'

'Yes,' hissed Derek, pushing back against the cock laying between his ass cheeks, making it slide up, away from his hole. He whined. Pathetic.

Theo thought about teasing some more, but as far as he was concerned, this was about his pleasure, not Derek getting his jollied. Lining up, with one long quick glide, he bottomed out. The grunt the tight slide pulled from him was drowned out by the yelp startled from Derek's lips. Beside them, the snoring had stopped, and after a moment a snort rang out in the now silent room before Stiles flipped over, now facing where they were fucking beside them. For a moment Theo thought they'd actually been caught, but the movement settled, and rhythmic wheezing breathing resumed. For once, he was more concerned than Derek who, whether through the collar, full ass, or entire situation, didn't seem to care. The insatiable slut just kept rocking back onto Theo's cock, trying to get some movement across his prostate.

'That's it slut, don't even care we nearly woke your husband.' Theo began long slow strokes into the tight hole as he egged the cheating slut on. 'Can't stay quiet with big raw cock in your cunt even when he's sleeping next to you, bucking back onto me trying to get it harder.' The slow pace continued, almost uncomfortable, but worth it when Derek began to let out little moans and whimpers.

'Please, Theo. Fuck me harder, make me feel it. I need it.'

'Such a dirty cheating slut Derek. When Stiles finds out he'll be devastated, won't he? But you keep begging for more.'

'Yes,' Derek sobbed. 'It'll kill him.'

Picking up the pace, Theo decided to go for the proverbial jugular. 'And when you get thrown out on your ass. When everyone knows what a cheating bastard, you know what I'm going to do, don't you?'

Crying now, but meeting every thrust, pushing his ass back slapping into Theo's hips, Derek hissed, 'yes!'

'Tell me, Derek, tell me what I'm going to do when you've ruined your marriage?'

'Mmmm, Theo. You…ahh,' a gasp cut off the words as the angle changed and every stroke bashed against his prostate. After that, every word was staccato and too loud. 'You'll get bored of me, you'll leave, you can't make me cheat when I get dumped.'

'That's right Derek. Right after you get caught begging for me to breed your cheating cunt and I've wrecked your perfect marriage, I'm going to tell you to fuck off. I'll go out and find another pathetic pretty boy who got married before he knew he was a filthy cock whore.'

'Gonna cum, Theo,' Derek mumbled, choked up. His head was in his hands, pressed into the mattress with his back arched and turned up. Nothing was even touching his dick.

'So responsive, going to cum untouched just from hearing what a pathetic cheating cum dump you are, big cock stretching out your cunt.' Bucking so hard into the tight pussy that his hips hurt and there would probably be bruises, Theo knew what would push Derek over the edge. 'I'll cast you aside and find someone new, in fact, I've already decided who. I was stroking my cock under the table all through their wedding reception just thinking about it. The icing on my home-wrecking wedding cake? She's Stiles' best friend, isn't she, Lydia? Fuck imagine when I bend him over rip open those tight tan deputy pants and nail Jordan Parrish. When I'm done with him the two of you can get a crappy apartment together, turning tricks to keep your sloppy man whore pussies dripping with cum.'

It was enough. The tightness around Theo turned to a vice-like grip. The hole began to flutter and pulse as Derek started to shoot into the sheets without any direct stimulation to his cock. As his own orgasm burst forth, Theo knew he'd found a veritable slut to liberate this time from the confines of societies expectations. Derek, Parrish, and Chris before them. They weren't meant to be tops, or straight. Their holes were for fucking and their cocks for decoration. Theo was a good Samaritan, he told himself as his cum continued to flood inside Derek. Helping people realise their proper purpose by lifting them out of the unfortunate circumstances in which they found themselves. So what if he waits until after they were married to tell them?

Without even pulling out, Theo climbed onto the bed, shuffling Derek further up so they could lie down, tangled together and connected so intimately, looking at the sleeping man next to them.

'Derek?' Stiles mumbled as they settled, eyes drifting half-open. 'What you doing up?' Theo held his breath.

All sense of propriety was still missing from his brain to mouth filter. Derek replied, 'I was so hungry, needed some filling. Got my doughnut creamed.' Theo snorted quietly in Derek's ear as he began to pump his hips.

Stiles frowned as though his sleepy subconscious knew the words were wrong but went back to sleep after he mumbled, 'okay. Love you.'

'Tell him you love him too, Derek,' Theo whispered, grinding his semi-hard cock deeper.

'Love you too, Stiles,' he gasped. 'Go to sleep, babe. Fuck me, Theo! Fill me with another load.'

They rocked together, writhing and twisting, kissing and sucking at whatever flesh they could find until for the second time Theo spilt inside. They both drifted off to sleep soon after.

A shuffling noise, a bang, some scraping, all conspired to wake Theo on the wrong side of the bed. For a moment he was confused, but when he saw the zombie-like Stiles moving about it flooded back. This time they had to be caught, Stiles even looked up and right at them, but either tiredness or cognitive dissonance gave them a pass as he just moved on into the en-suite. Before he could decide whether to stay or make a break for it, the fat hairy ass, full of his cum and still plugged up with his flaccid dick began to grind back against him. If they were going to get caught now, it was going to be in style. Once he was at full hardness, Theo manhandled Derek into a reverse cowgirl position, letting him grind down and ride the calm trot of his thrusts for a few minutes. Then, when he heard the shower cut off, Theo began a brutal pounding, hips lifting and dropping apace. Reaching around, he took hold of Derek's nipples each between a thumb and finger and pinched hard. Once again it caused the wanted reaction, a slut bottom cumming untouched. Theo followed not long after, dumping the third load inside. As his faculties returned, he pushed Derek off him and went to unbuckle the collar. It was hilarious. The second it came off Derek's dopey grin fell away. Replaced by the regular guilty look, it was tempered with panic as he realised Stiles was awake in the next room.

Rising from the bed, gathering up his scattered clothes and dressing, Theo stood leading in the bedroom doorway. A smirk spread across his face at the growing panic on Derek's face, even as his dick began to chub up, sat frozen on the bed.

'Hey sleepyhead, you look exhausted,' Stiles said, walking back into the room, a large towel wrapped around him, hiding his meagre assets. Was it any wonder Derek wanted to cheat on him? As he moved to the dresser, Stiles stopped, and a kiss was planted on Derek's lips. 'Even though your mouth tastes like ass.' If the idiot turned around, he'd find out he was being cuckolded by his best man.

Derek never broke eye contact with Theo. 'I love you,' he said full of emotion and entirely sincere.

Theo grinned. Just another loser who knew Theo was there to ruin their life and leave them in the dirt, falling for him like always. With a jaunty salute, he turned and slipped out, not bothering to close the front door as he left. As Theo climbed into his Mustang bought for him by Chris, the last guy whose life his dick had "liberated", the decision was made. The happy couple would be on vacation soon, that's when he'd install the cameras. Out of shot, he'd watch as a hooker bred Derek raw in his marital bed then plant the videos on his cell phone. Theo would be in the clear, Derek would be free, and Stiles always punched above his weight. Maybe best man Theo could get a twofer, no point rocking the boat.


	16. Day 15 - Prostitution | Armpit | Massage

**Summary for the Chapter:**

> Derek goes to an appointment hot and sweaty. It's an easy ride; he gets a tongue bath a massage and a happy ending. And no laundry to do at the end of the day.

**Notes for the Chapter:**

> Prostitution, Armpits, Massage, Sweat, Licking, Hand Job, Rimming, Jock Straps

Finishing up a brutal workout, Derek packed up and left the gym without showering or even bothering to wipe away his sweat with a towel. Muscles aching, shaking slightly from heavy lifting, he set off the few blocks to his next appointment. The afternoon was booked out for one of his more weirdly pleasant clients, Mr David Whittemore. What he wanted was a bit odd, but nowhere near the worst thing that Derek had been asked for.

Sweat was still beading on his forehead as he entered the lobby of the swanky apartment building. Without fanfare the doorman waved him to the elevator, his face by now familiar on Thursday afternoons. As the little box slowly rose up the three floors to his destination, the ripening sweat in his pits and balls filled the small space making his nose twitch.

'Mr Hale, please come in,' David said. Dressed in too-small shorts and a polo, knee-high socks and tennis shoes, Derek thought the guy looked ridiculous. But hey, who was he to judge? The guy could dress however he liked as long as it paid well enough.

'Hey, Dave,' Derek said, pushing past and dumping his bag. The last time he'd been here, there was a lecture on the reasons for shell cordovan's expense. So to Derek, the leather recliner was an excellent place to plant his sweat-dampened ass.

David stood in a trance, nose tipped up sniffing the air, the front of his shorts beginning to tent out. Snapping back to reality and smiling when he caught Derek lounging on his favourite chair, he said, 'you lot hot, Mr Hale.'

'Very, I'm sweating like a pig, and I stink.' He did. And he was; the heating in the apartment seemed to be on full blast undoing any cooling effect the walk over here had accomplished.

'Well, the spa is all ready, Sir. We'll get you all cleaned up and work on those sore muscles of yours.'

'Lead the way, Dave,' Derek replied, standing. Where his arms and legs had been in contact with the pricy leather, a glorious ripping sound rang out as he peeled his damp skin away. The tan leather was stained with the dark shape of his sweat sodden ass and back. Maybe it would be permanent. David just whimpered and licked his lips.

As they made their way to the room set up for these activities, Derek began to peel off his sticky clothing. First came the stringer vest, peeling it up and off and throwing the ripe damp balled up fabric at the back of David's head. They left little to the imagination, showing off his rounded shoulders and most of the shifting muscles in his upper back. Men and women drooled and tripped over their feet in the gym when they caught sight of his round pecs through the spilt sides, or a frequent nip-slip occurred. Derek was proud of his muscle and his body hair and wanted everyone to see it. A cough caught his attention, and he snorted at the sight of his current client stood next to the massage table, cock hard and leaking through his little white tennis club shorts, sweaty vest pressed to his nose.

While there was some fun in treating David like dirt, it was a secondary requirement. Derek knew his client's needs came first, however much the inclination to indulge was when such a pathetic specimen stood before him.

'Come on, Davey, time for my bathing, then you better give me the best massage you've ever given. I did a superset, and I'm hot, filthy, and sore.' The sore bit wasn't right, not any more, not really. Derek's werewolf healing had pretty much already seen to that. It was still pleasing to be on the receiving end of an expert massage. And he was getting paid for it.

David was impatient today, pushing Derek back slowly until his ass rested on the massage table. His arms were lifted and bent, hands resting together on the back of his neck. Derek pulled his elbows back and pushed his chest out, keen to show off his swollen pecs while he presented his rank armpits. A few cursory licks caught beads of sweat rolling down his chest, but the aim was the concentrated odour of his underarms. The left one came first this week, a tongue swiping through the hair, pressing hard into his pit. David's hands began to wonder, tangling in the hair of Derek's chest and belly, slipping over the damp skin, and digging into muscle.

It always relaxed Derek as the probing tongue sought out the salty bitterness coating his flesh. Usually, one side would keep David occupied for at least fifteen minutes. This time was no exception, the clock on the wall signalling twenty had passed when kisses began to travel over Derek's chest. The path was interrupted by each nipple being sucked for which he allowed low groans to escape. His tits had always been hardwired to his cock. David repeated his feast at Derek's right pit then pulled back, face wet, lips swollen, and hair a mess.

'Well, Mr Hale, let us move onto your massage.' David kneeled and removed the low-top Chucks releasing the stink of hot moist sockless feet. David didn't care, just began to knead the arches and flex the ankles. Before moving up, he signalled for Derek to stand and slowly peeled down the still sodden grey Jed North Rebel shorts which were plastered to his quads like a second skin. As they passed over the swell of his thick rump the waistband of his three-inch black Bike jockstrap, then the amply filled pouch, and the straps framing the underside of his behind. The combination often led to the shorts riding up and the straps being on full display during squats and deadlifts. Nothing was left to the imagination as people stared. For his part, David's nostrils were flaring at the concentrated musk.

'On the table please, Mr Hale,' he said, breathy and affected.

'Sure thing Dave. Hope I'm going to get a good rubdown today, better be worth every penny.' Derek laid out on the table, head poking through the padded hole at the top. The jock always stayed on until the last minute.

'Oh, it will be, Mr Hale. I assure you.' Warm hands, slicked with oil, began to work their way back into the arches of Derek's feet. Once he was moaning appreciatively, thumbs worked their way up the backs of his lower legs. Pressing in, hard and deep into his calf muscle, they were loosening him there and stiffening him further up. The swipe of a tongue began to join in with the skilled fingers, tasting the mixture of his skin and oil. It added the scent of saliva to the mix that his sensitive nose was able to pick up quickly. If the human could smell it, if that formed part of the appeal, Derek never asked.

The backs of his thighs, mostly when fingers skirted under the straps of his jock, teasing but not encroaching, were one of his favourite parts. Feeling the slick slide of hands digging into his hamstrings, the pull of his abundant and oil matted hair sparked that bit of him that enjoyed the tinge of pain. It always brought Derek to the point of leaking into his pouch, where he was uncomfortably pressed into the bench.

Ass skipped, as always, the journey continued, thorough. And, were it not for the constant slide of a tongue tasting his sweat and worshipping his muscle, it could be mistaken for professional. If ever David Whittemore's more unusual proclivities were to catch up with him, or he otherwise got disbarred, he could be gainfully employed at a spa in an instant. Though he'd more than likely prefer to take a job as one of the 'masseurs' Derek counted as colleagues. They could stick their tongues where they liked and get tipped for it, rather than fired.

The neck and shoulders, Derek believed, were purely for his benefit and relaxation. It was as if David didn't really get anything out of it himself, but was determined to fully follow through on a complete service. Soon enough though his attention turned back to Derek's ass. Kisses, licks, firm kneading that had an almost constant low groan droning out for nearly fifteen minutes ramped up the heat in the room. The licks got longer and harder as Derek was spread open, forcing their way inside, tasting the strongest sweaty musk available. Well oiled fingers joined in, rubbing around the rim before slowly pausing in and bending down. This particular massage technique always seemed to undo the previous work at relaxation, mainly as it ceased plenty of time before the inevitable conclusion.

Derek was well aware of the drill at this point, grunting in frustration but turning over onto his back. Stretching the pouch to the limit and lifting the heavy-duty elastic strap from his belly, his cock stood pointing straight up, each twitch adding to the liquid oozing through the black cotton. David ignored it, just started working his way back up from the bottom, skirting past the danger zone and moving onto the midriff.

Sensitive sides were always an issue growing up, before the bulky muscle when Laura could beat him in a fight. The anticipation of tickling ever came but was never realised, his abdominals and lats simply turned to relaxed goo, like the rest. The ever-present tongue dipped into his navel, and his peaked nipples were sucked into a hot mouth, lightly bitten, the hair around them tugged on. Derek lifted his arms to rest his head on his hands, presenting the matted dark swirls of his pits, their time together building to a close.

David would take one arm, massaging carefully from shoulder to fingers before placing it back in its folded position before licking and sucking, taking his fill of the exposed underarm. The other side would follow and then they moved onto the finale: Derek's happy ending, and David's main request.

The jock was peeled down slowly, Derek doing little to assist the struggle, not bothering to lift his ass or legs. His cock was pulled down in the battle. It sprang back up to splat against his waist, spraying sticky clear liquid that had pooled under the skin up across his chest. Oiling his hands and rubbing them together to warm them, David moved closer. Slowly he began the final massage. Stroking Derek in long tight swiped, he pulled the foreskin to pop over the ridge of his large mushroom-shaped glans on each downstroke.

On the reverse stroke, the skin would bunch up until David's fingers pressed it against the same place. It would pop over, covering the head again, squeezing out the copious flow of precum Derek produced and making his hips rise as he hissed. The man was an expert, even Derek's own hand couldn't play his cock lick this, and he knew it inside and out. Slowly but surely the ever-growing pressure built until finally, it burst out, spraying load after load of hot cum into David's cupped and waiting palm. Once the last drop was squeezed out, he made his way back up to Derek's head, slowly rubbing his hands together.

The bleachy stick of his own spend filled Derek's nose at it was slowly rubbed into his pits. It was rhythmic and consistent, little circles starting in the centre and spiralling out. Once satisfied with the results, David would ben over and suck the residue back off. 'I hope you were satisfied with your massage, Mr Hale. We'll see you again at the same time next week.'

Derek got up, ignoring David licking his own hands and his discarded clothes scattered over the floor. He left the room and headed to the master bedroom and the walk-in shower. Whether his client ever got himself off, or just ignored the bulge in his shorts, Derek neither knew nor cared. Over the pulsing jets of water, as he scrubbed himself clean, not incriminating sounds reached his ears over the sound of the shower. Once satisfied, he left the bathroom dripping on the carpet and picking up the towel left on the bed; that would be discarded on the floor. If this was a spa, then it was the staff's job to pick up after him.

Naked, he wandered back to the small entry hall of the apartment. On the dresser, there were two crisp new hundred dollar bills. Next to them, a brand new stringer vest, mesh this time. Smirking, he opened the packet and slid it over his head. The Nasty Pig jock followed, then the mesh Tracksmith running shorts which were so short he wouldn't even have to bend to show off the jock's straps. The tank came down lower at the back. Admiring himself in the mirror, he realised it looked like he didn't have anything on the bottom half at all from behind. Maybe he'd even catch some trade on the subway looking like this. Slipping on the brand new Converse, he left for the week. It wasn't a bad gig, even if the pay was a bit stingy, it came with a free massage and a few hundred bucks worth of new gear that had him looking fuckable. And he didn't even have to do laundry.


	17. Day 16 - Fucking Machine | Feederism | Intercrural Sex

**Summary for the Chapter:**

> Stiles can’t reach Dereks hole any more with his dick so there’s an extra long dildo being fucked into him while Stiles lazily fucks in between his soft thighs. Every time Derek swallows a mouthful Stiles is there with another bite or the straw from the calorie shake leaning his weight into Dereks flab as he tells him what a hot blob of lard he is.

**Notes for the Chapter:**

> Fucking Machine, Feederism, Intercrural Sex, Obesity, Feeder Stiles, Fat Derek.
> 
> Massive fat gain and feeding. Skip it if it's not for you, otherwise enjoy a very massive Derek ;)

When they started this, neither of them really realised how far it could go. A werewolf could take a lot of punishment without any ill health. It meant all the preoccupation with Stiles' father's health didn't translate to Derek. Derek, who could now only stand with Stiles assistance.

Stiles loved cooking but always had to be careful to make sure it was healthy and lean. No buttery sauces or fatty cuts were in his repertoire when his dad could access it. When they started dating, there was nothing Stiles loved more than spending a night in at the loft, cooking, talking, and laughing. The looks of ecstasy that fell over Derek's face when he tried a new recipe just made Stiles want to feed him more. The first time Derek let out a pornographic moan at a soufflé made Stiles reassess precisely why he enjoyed feeding Derek so much.

One day, over-stuffed and belly swollen, looking at Stiles and knowingly sniffing the air, Derek grinned. It turned out he wasn't averse to the prospect of being fed up if he got to eat such delicious treats. What started as one bite too much and hard convex curve to his abs quickly led to a growing Derek. Stiles now had detailed meal plans with specific caloric requirements, and Derek's meals were specially prepared to focus on energy-dense fats.

Derek had eaten dinner two hours ago, a family-sized casserole dish of lasagne, topped with half a pound of creamy cheese. An hour ago it had been dessert; a whole steamed suet pudding topped in luscious brandy cream. Now, time for his first evening snack, he slurped on a six-thousand calorie shake of heavy cream, peanut butter, maltodextrin, and ice cream.

After the evenings heavy eating was done, his bariatric chair was wheeled into the bedroom. Derek continued to sip away at the cold sweet liquid while Stiles set up the hoist. Slowly and carefully, the massive weight was transferred. Then the fuck machine was set up, a greased up dildo blindly positioned at the hard-to-reach hole and switched on to begin pumping in and out of Derek.

Derek relied on the machine these days. Massive plump breasts sagged down onto a vast protruding belly, maintaining a fold even as he lay down nearly flat. It spilt out to the sides under its own weight, almost doubling his width and drooping to rest on the bed, a testament to Stiles dedication to keeping him filled.

The machine held a two-foot long piece of flexible silicone that rarely hit more than six inches inside of him. Stiles couldn't fuck him any more, ass too big and legs too heavy to allow entry to his asshole for the real thing; no longer able to support himself on hands and knees. Besides, Stiles had pointed out the first time they had used the machine, this was Derek could keep eating, and there was someone free to fetch him snacks if he ran out. It was a good argument.

Now, Stiles perched on his thighs, fucking into the soft fluffy fat between his legs. As the desperate slurps from Derek's emptying shake cup got louder signalling the need for more Stiles came, noisy and messy.

'You're doing so well today babe,' Stiles said as he recovered his breath. 'Isn't your belly sore?' Kneading at the flesh and pressing into the swollen area where Derek's distended stomach lay drew groans and a massive belch.

'Always sore, always hungry for whatever you give me.'

Stiles pulled out a can of whipped cream from under the comforter with a wink. 'Pull you gut up babe, let me see your pad.' Derek complied, gathering as much of his bulk as he could with his wobbling arms and exposed the thick pad of fat that made his one large cock look much smaller. Not that he ever saw it himself anymore.

Slowly, Stiles began to stroke him, pushing blubber out of the way to manage his grip and quickly jerked Derek off. It brought him close. The machine pounding into his prostate assisted, but these days it always took a little bit more, something special to get him off. The nozzle of the cream-can pushed past his lips, and Stiles held down the button. Gulp after gulp, the fluffy whipped dairy treat went down, over and over until his belly was ready to explode. Then the container sputtered as it emptied. It was his dicks turn to erupt then. Cum sprayed over Stiles, and between his thighs, and tired he released the hold on his belly, letting it flop back down to wobbly and eventually settle.

For a while, he'd nap. The smell of supper would wake him, and Stiles would make sure he ate well again while he had a wash. In the morning, he'd get bacon and eggs, and French toast; all covered in syrup—growing a little more humongous each day.


	18. Day 17 - Threesome/Orgy | Master/Slave | Titfucking

**Summary for the Chapter:**

> Derek is trussed up, arms tied to his sides and squeezing his pecs together, one after one Stiles invites the rest of their pack to fuck his tits and mark him up.

**Notes for the Chapter:**

> Orgy, Master/Slave, Titfucking, Bondage, TPE, Total Power Exchange, Dehumanised, Full Time Slave
> 
> This is the first fic I've had that's gone over 10K hits, I know that's not really a great metric to measure engagement but to everyone who has read, commented, or left kudos, please enjoy the next chapter and feeding my ego with glowing praise ;)'
> 
> (Or constructive criticism)

There was a total power exchange between them. In their home, Stiles' word was absolute, and Derek obeyed. It suited Derek's need to let go of responsibility and hand over responsibility to someone else. Outside they weren't in your face with it, but Stiles was the boss. He picked Derek's clothes, chose his meal orders, agreed on his behalf to social activities. Only Derek's work was off-limits by mutual agreement.

It meant that at home, Derek was not 'he' but 'it', not 'Derek' but 'slave' or 'pet', not clothed but naked always. There was an amnesty when the Sheriff came round but not for their friends. Its responsibility was to treat them as if they were master too. There were rules, and it was allowed to report to Stiles if they were ever broken. Everyone knew going in how their household operated. If they weren't prepared to be involved, then they would meet somewhere else. It surprised neither of them that Lydia had been the most receptive to the situation. She didn't seem to get any sexual pleasure from it. Instead, revelled in its naked statuesque beauty as it gave her a pedicure, played footstool for her tired stilettoed feet, or holder for her wineglass.

Tonight was the boys' game night. That meant it would be busy working to keep them happy then have some pre-planned reward of a sexual nature. Revelling in being used as they all got off on it. As the evening was coming to a close and one after another began making noises about making tracks and getting their rocks off with the final entertainment. Stiles kicked it out from under the table where it had been nursing on someone's cock. Pet didn't really know who's, nor did it matter.

Ropes were brought out, and its arms were tied to its sides, the pulled forward, squeezing its chest. The result of massive pecs pressed together was that it now sported a respectable cleavage. It was ordered to lie down on a bench and stay there until everyone had fucked a load out between its titties.

One after one, the men stood over it, cocks slipping into the crevasse in its chest pointing towards its feet. Their asses would rub over his face as they began to thrust, bashing its nose and chin. Some of them took the opportunity to sit, cutting off its air until it locked inside them until they were satisfied. Master wasn't angry the first time it happened, just clapped and laughed, so it made sure to rim as well as it could, digging in deep.

Each time the thrusts would get faster, then the splash of cum hitting its belly could be felt. Each one stood then pushed their spent cocks deep into its throat, leaving them until they were clean and shrunken back to their flaccid state. As each man used the slave, they'd give it a condescending pat then left. Eventually, only Master and Theo remained. Neither of them used Its tits, of any other part of it. Master just untied it and told it to clean up, then the two went off to bed together.

As it cleaned, it could hear the sounds of fucking, moaning and groaning, screams of ecstasy. I love yous passed between the two men. Its chores completed, the slave went to its cage in the washroom and curled up into the doggy bed inside, smiling at the thought of having a new Master to use it and order it about.


	19. Day 18 - Petplay | Humiliation | Bloodplay

**Summary for the Chapter:**

> Ethan had always wanted one of those big nasty dogs that kept everyone else away but was a sweetie to its owner. Unless its owner smacked it one too many times with a newspaper. So catching Jackson looking at pup play videos gave him an idea. Cue a mauling.

**Notes for the Chapter:**

> Petplay, Humiliation, Bloodplay, Breeding, Knotting, Pseudo Animal Cruelty, Mauling, CBT, Bloody Injury, Knotting, Situational Humiliation.
> 
> To incorporate bloodplay into a petplay fic, I decided to go the route of badly trained attack dog play instead of puppy play. No worse than the violence in the show, but sexualised. Skip it if that's not for you.

Ethan had always wanted a dog. One of the big mean, nasty ones. When he was younger, it was because he'd assumed it would be able to protect him and his brother. As he grew older, he realised it was more out of a sense of masochistic desire, having something that would fight against him violently. They kept everyone else away but were sweeties to their owners. Unless it's owner snaked it one too many times on the snout with a rolled-up newspaper.

None of those was a good reason to get a dog, though, and he wasn't dickish enough to get one when. He'd probably end up fucking it up. Cue Jackson, who was already beautifully fucked up, just like Ethan. On coming home one day, he'd caught his boyfriend jerking off to videos of men dressed up in dog masks. They were being led around on choke chains and plugs sticking out of their asses with wobbling rubber tails.

Once Jackson had gotten over his mortification, he realised that Ethan wasn't actually trying to humiliate him for his proclivities. They decided to explore their weirder kinks. Jackson admitted that the idea of being a pup appealed to him and as they'd always been rough in bed, Ethan's confession seemed to just rile him up. They fucked like rabbits that night.

Soon enough, the mask and the tail had arrived. Jackson's ass was wagging in anticipation even before they'd gotten the boxes open. Soon enough, the dog hood went on. The bottom was left open so that his jaws were free and his teeth lengthened with a limited shift to complete the look. Ethan carefully attached the collar and pushed the colossal plug inside, giving a couple of tugs on the thick rubber tail for good measure.

'Who's a good boy?' Ethan cooed as the transformation was complete. Jackson bounded around in all fours, jumping and licking, surprisingly lost in the moment.

'Who's my good boy Jacks? Not you.' Jackson stopped his licking and whimpered. It was part of the plan. They both knew that to some extent, he was going to take elements of this to heart. 'You're a naughty dog, always biting and scratching. Ruining the furniture and pissing on the carpets.'

That was when the growling started. It didn't take much goading or humiliation for Jackson's temper to surface, but he didn't break character. This wasn't the temper of a petulant narcissist, but an angry dog that was beginning to feel backed into a corner.

'Bad dog,' Ethan roared, whacking at Jackson's face with a magazine he'd picked up and rolled into a tube.

The growling stopped as a high pitched yelp of surprise and shock released only to start again, lower and more dangerous. Ethan leant over, reached down and squeezed at espoused balls as he laughed out, 'maybe getting you fixed would…' His scream of pain cut off his words and they both backed up.

Both of them stared at each other, breathing hard. Ethan cradled his bleeding arm too shocked to chastise. Jackson had bitten hard into his flesh, tearing the skin and leaving copious amounts of red dripping out, falling to the floor. Shuffling from side to side and whining Jackson looked, for a brief moment guilty where he'd slinked back across the room. Then his head rose, and he began to sniff, gaze moving to the front of Ethan's shorts.

Jackson stalked forward, but the wall behind Ethan meant he had nowhere to go. A snout jabbed painfully into the bulge in his shorts before a jaw clamped down over his package making his pulse race and precum ooze from his slit. This wasn't where he thought jaws would end up, but the more breaths he took to steady himself the more he throbbed and the tighter the clamp became with the sharp press of canines sparking nerve endings desperate for more.

'Useless fucking mutt!' He cried, bringing the tube of glossy paper down on the pup's back over and over. 'I should have dumped you off at a shelter and let them deal with your endless whining and anger issues, get the fuck off me,' he roared. It turned into a yelp and teeth cut into the flesh in his most sensitive area. A kick to Jackson's ribs caused the jaws to release, and Ethan looked down to see the torn fabric, once grey, now soaked red, tented out by his solid steely erection.

Once again, the growling picked up, and Ethan knew he wanted to lose this fight badly. He ran. Ten steps across the flat, maybe twelve then the weight of a pouncing Jackson hitting his lower legs sent him sprawling to the ground, razor-sharp teeth cutting into his right calf. As he kicked and struggled claws raked over his skin cutting through flesh and clothes, covering them both in the tacky feeling of blood.

Teeth sank into the meat of Ethan's rump, and he stilled, whimpering. The back of his shorts was shredded open, and the weight over him shifted until Jackson covered his back. Something hot and hard began poking at his ass painfully jabbing even as he rose to his knees to offer himself up. Jackson's jaw closed over the back of Ethan's neck, demanding compliance and holding him in place.

'Jacks,' Ethan cried. 'Good boy, Jacks. Show me who's boss. Take your bitch.'

Blood trickled down his face, and he licked out as it reached his lips. The taste made his buck back onto the painful stabbing, finally finding its mark as he became speared on rapidly pumping cock. Taking his role to heart, Jackson's jaws clamped down harder on Ethan's neck. As his hips bucked wildly, chasing completion without any care for his bitches comfort the pounding intensified.

Ethan sobbed and begged, for harder, for it to stop. When Jackson started to grunt, and something kept bashing into Ethan's are hole, he knew it was nearly time.

'Come on, Jacks. Breed your bitch. Force your big knot in and tie us together. Make me yours.' The breath was knocked out of him when the firm bulb of flesh forced its way through. His hand found its way into the rags of his shorts, violently stripping his sore dick, using the drying blood as lube. At the same time, taking his role very seriously, Jackson began to turn and started walking away. Ethan had no choice but to follow. Sobbing, he came hard, the painful tugging at his battered hole and degrading situation too much for him to hold out longer.

They settled, Jackson beginning to lick them both clean of the blood that coated most of their bodies until he was ready to slip out. Then he feasted on the mess he'd made.

'That's my good boy,' Ethan mumbled, exhausted and falling asleep. Whenever you're ready, your bitch needs breeding again.'


	20. Day 19 - Hate Sex | Cockwarming | Mirror Sex

**Summary for the Chapter:**

> Despite all that had happened Theo and Stiles were still always at each other's throats, only they'd come up with a pressure valve.

**Notes for the Chapter:**

> Hate Sex, Cockwarming, Mirror Sex
> 
> A short one to end the day. Don't worry, there's some longer ones coming up.

Despite all that had happened, Theo and Stiles were still always at each other's throats. Only now they'd come up with a set of pressure valves. A way to release the tension before Scott or Derek was forced to intervene, something that caused acrimony in the pack as people inevitably took sides. Scott had always had a blindspot for Theo and Derek trusted Stiles above all others. It led to weird fracturing of their group, and they were careful not to let their own needling of each other reach that point.

This was Stiles favourite method. He was glad he'd grown out his hair.

As Theo pounded into him from behind, he'd run his fingers through the long strands, tangling and gathering them in his fist. Then, pulling back hard, it forced him to look into the reflection of Theo's eyes. Mirror sex with an actual mirror. Bile would spill from Theo, every cruel and humiliating thing than ran through his head, always cutting and hurtful. It was a toss-up every time whether the words or the stinging pain in his scalp would have Stiles crying first.

Once Theo had cum he'd let Stiles' head drop as he admired himself in the mirror, flexing and squeezing his sweat covered pecs. Allowing his cock twitch inside, keeping warm until he was ready to fill Stiles up again, the two stayed connected together.

Thanks to his length and being a shower, it never shrank enough to pop out unintentionally. Sometimes it would stay there marinating for hours as Theo lost himself in a narcissistic rabbit hole.

Usually, he wasn't that self-absorbed, Stiles knew. It just prolonged the humiliation, which made the whole thing so much better. Infinitely in fact. Usually, it was him that began backing up onto Theo's hardening cock where it was buried inside him. Too desperate for a burning ring and the sting of hair being pulled to wait for Theo to begin.

After the second or third breeding, Theo would begin to lose interest, too mellowed out to maintain the distaste that stopped them from acknowledging more pleasant emotions. Theo would sleep on his back, turned slightly. Stiles would curl up under the covers, mouth full of their combined and concentrated taste. The warm heat usually meant Theo didn't have to get up, and Stiles always woke hydrated.

Whoever woke first always left, regardless of where they were, so the other one would wake alone. Next time would be Stiles' turn. He favoured bruises that were deep enough, even accelerated healing struggled to remove them overnight.


	21. Day 20 - Noncon/Dubcon | Foodplay | Creampie

**Summary for the Chapter:**

> Theo agrees to some foodplay, but when his face is shoved into Liam's hole and he starts to push out cum it's not the creamepie Theo was expecting. Liam tells him how Stiles was more than happy to make it for him once he knew it was Theo who'd be eating it all up.

**Notes for the Chapter:**

> Noncon/Dubcon, Foodplay, Creampie, Forced, Felching, Throat Fuck, Manipulation, Cum Farts
> 
> Sex is consensual but it turns into a specific sex act for which consent is explicitly refused. Please skip this chapter if Noncon is not for you.

Convincing Theo they should add some food play into the mix of their tenuous fuck buddy situation was the hard part. Convincing Stiles to fuck a couple of loads into him, Liam found was the easy part. Not that fond of bottoming, Liam just grinned and bared it for a worthy cause and Stiles laughed the whole way through, eager to get one over on Theo.

'How about a cream pie?' Liam asked, whipped cream in his hand, serene smile on his face, knowing what was coming next. He'd perched himself behind Theo's head on his knees to give himself the best chance of pulling this off.

Theo looked unsure. 'What? You mean in my face?'

'Uh, huh. I'll spray it all over and then make you lick it all up, it'll be fun.' For me, Liam didn't add.

'Okay,' Theo said, unsure, and at length. 'Gimme your cream pie.'

Liam could pinpoint the exact moment Theo realised, but by then it was too late. The kind smile had slipped from his face replaced with one of pure mischief.

Before he could fight back, Theo's arms had been held down, and Liam's ass was forced down over his mouth. The crack was rubbed over his nose and pressed down hard. Eventually, he'd have to open his mouth to breath, unable to wrestle the well-planted bulk off.

The first wet fart made him buck and struggle harder, but Theo didn't have the strength or leverage to throw Liam off. Besides, if the bearing down over his pursed lips or constant dripping onto his neck was anything to go by; Liam was getting off on Theo's struggling. Liam knew Theo didn't want this but wasn't stopping. So. Why did that excite Theo?

A fire burned in his chest, agony radiating out as fingers pulled with supernatural strength on his sensitive nipples. Theo opened his mouth to scream, too late realising the ploy. Old cum splattered out of Liam's rippling ring, dripping into his mouth.

As Theo began to cry, his tongue shot out against his will, licking into the messy depths, tasting more, searching for another dollop of bitter cream.

'That's it,' Liam cooed. 'I knew you were a dirty fucking cum whore like me. Force-fed Stiles' cum and you're digging around in there for more of it. Such a slut.'

Every time he let out a choked sob or his tongue poked in deeper, Liam would grind down harder onto his mouth. Theo was so hard it hurt. Whether it was being used, degraded, or the pain in his chest, he didn't know, but as Liam farted another large mouthful of Stiles' cum from his hole Theo choked on it. Then, untouched, he came, exploding with enough power to hit his neck and probably Liam.

'Would you look at that,' Liam said, teasing. 'Such a whore you get off on this. Well, now you can get me off.'

With that, he shuffled back, giving Theo a split-seconds relief that it was over. Only for Liam to coat his dick with the chocolate syrup they'd been using earlier, then shove himself balls deep down Theo's throat. The sweet and salty flavours mixed on his tongue as he began to choke and splutter resigned to having his face fucked, the smell of sweaty balls filling his nose.


	22. Day 21 - Size Difference | Exhibitionism/Voyeurism | Impact Play

**Summary for the Chapter:**

> Corey hurries to he loft to get in place for the weekly show to start. While they're the same height, Derek is twice as wide as Stiles and for the last few years he's grown, muscle and fat. The size difference is striking and Corey thinks it gets bigger each time. He’s already naked, running through town like that. Derek's chained up to the ceiling. This time it’s different.

**Notes for the Chapter:**

> Size Difference, Exhibitionism, Voyeurism, Impact Play, Big Bulking Derek, Dom Stiles, Sub Derek, Edge Play/Risk Taking (for the way Corey approaches exhibitionism)
> 
> Noncon/Dubcon voyeurism - the people being watched are aware but the watcher thinks they aren't

Late. He was late. Corey hurried, running along the road and darting into the industrial-looking compound that housed Derek's loft. They'd be starting soon, and he needed to be in place first. The weekly show started at the same time, and there were only a few minutes left.

While they were the same height, Derek was twice as broad as Stiles, and over the last couple of years, the size difference had only grown more stark. Derek's muscle mass had developed considerably, and as it turned out, his leanness was the product of stress and vigilance. Relaxed and happy Derek was…rounder. Stiles was still what he claimed to be one hundred and forty-seven pounds of fragile skin and sarcasm or something like that.

The size difference was striking, and Corey swore it got wider every time he watched. It wasn't the only difference in size that the pair sported.

Already naked, Corey slipped in through the sliding door, thankfully not fully closed. It was a lucky oversight for him on the part of the evening's entertainment. It was why he usually arrived early before they did. Stripping at home, he'd turn invisible then make his way to Derek's. The most direct route took him through the busiest parts of town, past the Sheriff's Station. The thrill of his control slipping while making his way there kept him hard the whole way. It would only worsen the humiliation if he became visible in the wrong spot. It was an incredible feedback loop. On his way home, he'd jerk off in the open, and he revelled in fear of exposure once the excitement from adrenaline and endorphins was worn off.

Derek was already chained up from the ceiling, hands shackled and raised above his head. It stretched out his massive pecs that when relaxed, were hearing the verge of losing structural integrity and becoming moobs. For now, the large muscles were winning the battle. His belly was round, and the stretch raising him to his toes was lifting it to look beautifully round. It was more beach ball stretched out muscle when relaxed, but over the last few months, an overhang had been starting to form.

The thickness of tree trunk thighs and that large gut, all covered in thick black hair now made Derek's dick look tiny. It wasn't, average really, but the man's size and growing thickness, the pad of fat at his groin, all swallowed it up.

Entirely hidden before he walked around Derek, Stiles was a fabulous contrast. Lithe, thin, muscled but a swimmer to Derek's weightlifter, four or five of him could have fit within his willingly changed victim. Even if in the unlikely event Stiles' weight ever bloomed, there would never be any danger of his cock being consumed. It was closing on a foot long and nearly as thick as the baseball bat he was so fond of. It always amazed Corey how well Derek took it. Slowly, quietly, he began to edge his own.

There was something different this time that Corey couldn't put his finger on, but it was raising the hairs on the back of his neck. The thrill of being caught in his voyeuristic shenanigans was more incredible than it ever had been before as he watched stiles go to the bucket of water. The tub held the soaking rowan wood switches. Why bother if Derek couldn't bruise? That was it he realised as the first whoosh of air sounded, followed by the beautiful smack of wood on flesh. Derek was looking right at him.

Usually, Derek had his head tipped down in supplication as he begged for more, or thrown back while roaring in pain. Never before had Corey seen him looking forward, biting his lip to keep from calling out. It was like Derek was staring straight into his eyes. Each time the switch landed every emotion, and the slight flicker of muscle that gave away the level of pain Derek was facing went straight to Corey's groin.

Stiles was not a light touch, and they were old hands at this. Each hit was expertly aimed at Derek's back. One to make him pull his shoulders, making them ache. Another landed just right to have him lift his considerably bulk up on the very tips of his toes. The one that followed in the crease of his well-muscled thigh and plump round ass surprised him into lifting his leg. It threw his balance, and the other toes could no longer support the weight. It left Derek swinging on the chains and gave Stiles the perfect opportunity to switch to a virgin switch. The timing was perfect and deliberate—a break caused by a necessary interruption that didn't break the flow. By the time Derek's feet were planted again, and his balance returned, the thwap of the freshly soaked wood returned.

Then, after Derek couldn't hold in his cries any longer, the beating stopped, abruptly. This was a departure too. Once Stiles broke Derek's stoic shell, he would eke out every last cry until they were both exhausted and it would take the weekend for the bruises to fully heal. Then Stiles arms wrapped as far as they would comfortably reach and he leant out, head resting in the sweaty mess of Derek's right pit. Joining him in starting straight into Corey's eyes.

It was apparent they knew he was there. Possibly, they could see him. He didn't know how; everything told him his camouflage was still up. The surer he was that this was it, the time he had been caught, the faster the hand on his dick moved. Stiles began to grin.

'It's not just the switches that are Rowan, you know. I put some around the door—made wards. You were careless last week, couldn't hold it, came on the floor. That was when we knew. Leaving evidence. We suspected before that though, Derek thought he heard things, but was always to far gone to be sure it wasn't all in his head. You look at us all the time, though. I think you think it's subtle, but it's not. Mason didn't want to join in, but he gave his blessing. You'll probably have to have a long talk with him when you get home tomorrow though.'

'Tomorrow?' Corey whispered, confused, but so incredibly turned on. Every fantasy of things he could never have all coming together in reality.

Like he hadn't heard the susurrated query, Stiles continued. 'The question is...do you want to take my place? Or Derek's?'

He was too close, had edged too far, and with a groan, Corey began to spill over the concrete floor of the loft. Quickly the reality sent in, and despite the tremendous amount of satisfaction that flooded through him at finally getting caught, having someone see, shame-filled him as well. His face burned hot, and the flush spread down his naked chest. Then he realised he'd snuck into their home, to watch them have kinky sex, and they'd caught him. They'd seen him burst. A sob passed his lips and Stiles' grin faded.

'Hey, little perv, come on it's okay. Come here.' It was soothing, and despite the name, his feet began to carry him. Corey threw himself at Derek's belly, and Stiles moved to squash him between them.

'I'd hug you back,' Derek began. 'But I'm a little tied up.'

Finding his voice, and realising that he really was invited to join in, Corey asked, 'can you show me? How to do it? Beat him, I mean. So it's good? Then...maybe I could take his place. I like the way it makes him scream.'

Stiles grin returned. 'So do I, baby.'


	23. Day 22 - Formal Wear | Overstimulation | Sadomasochism

**Summary for the Chapter:**

> Derek is bent over, tux pants ripped open sobbing as Chris’ stubble scrapes at his sensitive hole, can hear the whine of the taser , wolfsbane coated gloves squeeze his balls tight. After Chris leaves him a sobbing mess he can go through the door to Chris’ room for more, or down the stairs to leave with everyone seeing what he looks like. He doesn’t even stand, just crawls, a moth to the flame.

**Notes for the Chapter:**

> Formal Wear, Overstimulation, Sadomasochism, Sadist Chris, Masochist Derek, CBT, Electrocution, Chemical Burns (wolfsbane), Falls, Broken Bones, Beating, Pain Play, Consensual, Semi-Public Sex, Threat of Exposure, Threat of Humiliation, Rimming
> 
> All consensual but no punches pulled. This contains heavy S&M beyond what a human could endure.

They'd been teasing one another all night. Chris getting more frustrated each time, Derek knowing he was going to suffer more for it. Still, they continued to let it build. To be fair, it was Natalie and Noah's wedding reception, so it behoved them to put in a good showing before sneaking off. Still, at the earliest opportunity to begin, Chris pressed on the button for the shock collar that he'd been keeping in his tuxedo pants, instantly drawing Derek's attention. Then he made his way up the stairs at the back of the garden.

Once the burning subsided and he was reasonably sure he could follow without Chris shocking him mid-walk, Derek hurried after. It was next to impossible to keep the pain off his face when the electricity sparked through him. The shaking in his legs made him think staying upright would be beyond impossible. As he reached the top of the stairs, which led to the balconies of the suites in this particular block, his fate awaited him.

Chris stood there, tuxedo jacket discarded, his bowtie still on but undone. Shirtsleeves rolled up to his elbows highlighted the black leather gloves he wore, making Derek's pulse begin to pound. 'Against the balcony. Lean over. If you don't hold on and fall over, you can heal your breaks, come back up, and we'll start all over again.'

Derek obeyed. The concrete wall was the right height do dig painfully against his hipbones. The decorative steel handrail on top bore his weight, pressing uncomfortably against his bladder and stomach and digging into the bottom of his rib cage. Once his head dipped below the level of the rail on the other side, looking down a twenty-foot drop into thorn bushes, the weigh of his legs alone was no longer enough to keep him in place. Grabbing onto the rail meant no escape but down. He was exposed, completely and utterly to whatever torture Chris was in the mood to meet out. The wolfsbane infused gloved, with their palms covered in thousands of tiny sharp spikes, made him think it was going to be quite a ride.

There was no consideration to propriety this evening. No cares about how Derek would get to his own suite afterwards. The pricked gloves pressed against the rear seam of his tailored pants and pulled. Two hundred dollars of formalwear destroyed and his ass scratched and stinging, the poison guaranteeing his healing wouldn't stop the sting from lasting hours.

A click and a microsecond later agony spread though Derek once more. It almost caused him to lose his grip on the bar. The remote wasn't attached to a shock collar anymore, but the shocker had been repurposed. It was now attached to a metal plug that had been pressed into Derek dry at one end and a chastity cage which crushed him down into a tiny spike filled hell trap less than an inch long. It was a torture device pure and simple, designed not to correct behaviour, but to inflict the maximum level of pain. That Derek could, in a more comfortable position, endure it in public with only the slightest flicker over his visage was a testament to his exceptional control. And, of course, to his insatiable appetite as a glutton for punishment.

Panting by the time the button was released, Derek was ready to begin begging, and they were only minutes in. 'More. Please, make it hurt more.'

'Whatever you want sweetheart,' Chris responded, electrocuting Derek's most tender areas once more. Derek's masochistic tendencies demanded the services of the most sadistic mind he could find. That he could trust Chris, who revelled in perfecting the techniques of torture he'd grown up with but using them for their mutual pleasure, making them a perfect pairing. Chris had never enjoyed inflicting pain for the sake of it, but for a willing victim who'd beg for more? He flicked the catch on the remote so he could return it to his pocket with the juice still flowing. Then Chris began to rain slaps down on the exposed skin of Derek's behind, watching as tiny pinpricks of blood bead as the gloves did their damage. The battery on the shock device would only last a few minutes running continuously. Still, there were plenty of toys to escalate with. By the time it had run-flat, Derek's skin would be red, swollen, and sore for days.

The weak little werewolf was already sobbing by the time the involuntary muscle contractions, beautifully violent, ceased. 'Poor boy,' Chris whispered. 'No more battery. Don't worry, though.' The crackle of a taser made Derek grind his steel covered and crushed cock into the rough wall with as much force as he could manage. Taking advantage of the involuntary motion, Chris yanked out the plug while the ring of muscle was clamped down at its tightest. The resulting whimpers made him throb and leak. Derek responded to the most intolerable agony so well.

Ripping the torn fabric open wider, Chris was able to get one of his gloved hands in to release the rest of the device. Then pulled Derek's rapidly expanding cock to point down. Now exposed any movement would grind the delicate flesh into the wall. At least when Chris wasn't holding onto it in a tight squeeze, slowly wanking it with the spiked and wolfsbane infused glove. Ignoring the demands for more, he began to lick into the empty and now gaping hole, doing his best to irritate the damaged skin with his stubble. Suddenly, with his tongue buried deep, the muscle began to spasm around him and then Derek came hard and messy all over the glove irritating his cock.

It was inevitable at some point the pain would get the guy off being such a slut for it, luckily it just made anything further feel even worse. Chris let go his grip on the spent dick and began crushing the ball sack in his hand. Bored of the rimming, and tongue a little uncomfortable, he pressed the taser to Derek's perineum, released his ball bag and let the volts fly. Over and over, until he could smell burning flesh, Chris zapped at the back of Derek's balls.

On and off, randomly, unexpectedly, the electricity sparked, until Derek had hardened once more. Making shallow thrusts into the stone, rubbing raw the head of his dick just as well as if he's been using a cheese grater, he whined. Cumming was too much, and his hands shot out to grab his balls. As expected, he overbalanced, tipped over the edge and plunged down the long drop to be stopped by thorns. Chris wasn't sure whether to sigh in exasperation or burst out laughing. Instead, he just snorted and gather up his things and made his way to his room.

Humiliated and glad this part of the garden was somewhat cut off from the rest of the party near the main building, Derek rolled out of the bush. Staggering back towards the stairs, his broken wrist began knitting itself together even as he knocked it rhythmically against the jut of his him. The other hand was picking thorns out where they stuck into his trunk. The dress pants were barely holding themselves up, not that it mattered. Anyone who caught him would receive an eyeful of red, raw, ass cheeks and cock. Below that balls swollen and blue from bruising were pushed out proudly by his thick thighs.

The balcony was empty, but the door to Chris's room was open, light spilling out. Derek stumbled over and propped himself up against the frame, still favouring the right side of his ribs from the fall. Chris sat on the couch, not looking around.

'You can come in for more. If you do, you'll take everything I give you. Or, go down the stairs to your own room with everyone seeing what you look like.' Chris didn't even look up at him.

Derek liked pain, not humiliation, but he looked down at the ground wondering how much more he could take. At the sound of a telescopic baton flicking open, his eyes shot back up, bright and hungry. In Chris' other hand a cattle prod arced, crackling and promising pain so much worse than the stun gun could produce. The burning, bleach-like scent of ozone made his nostrils flare, and his tongue darted out, tasting the blood of a healed cut.

Barely able to walk, Derek dropped to his knees and crawled over like a moth to a flame, his answer clear. He knows he'll get burned; hopes for it. As the first strike of the baton fell, he breathed out a reverent, 'thank you.'


	24. Day 23 - DP | Tickling | Shower Sex

**Summary for the Chapter:**

> The last time Danny visited, Jackson pissed the bed. It was humiliating, and it stank, and it was so warm. He loved it. And so did they. The cleanup was a nightmare though. This time they used the walk-in shower and thank fuck for underfloor heating. Ethan and Danny Tickle Jackson until he pisses himself then they hose him down and both fuck him together against the wall.

**Notes for the Chapter:**

> DP, Tickling, Shower Sex, Situational Humiliation, Accidental Bedwetting, Kink Discovery, Piss
> 
> I honestly couldn’t think of a scenario where you’d have DP, Tickling, and Shower Sex unless the intention was to tickle someone until they pissed themselves. So bonus watersports. Maybe I lack imagination
> 
> ¯\\_(ツ)_/¯

The last time Danny had visited his childhood best friend and, incidentally, his ex-boyfriend things were a little weird. It was the first time he'd seen Jackson since the two had gotten together and it was…weird. Then it got weirder. Their apartment had a spare room where Danny was expecting to stay. The day after he arrived the flat above had a burst underfloor heating pipe which came through the ceiling soaking the extra bed.

Danny had offered to take the couch, Ethan refused. Ethan had offered to take the couch, Danny refused. Jackson told them to fuck off when they looked at him, he wasn't taking the sofa. Besides, they were all big boys who'd slept together in every two-person combination, and the master bed was huge. They could share.

It was awkward the first night—Danny and Jackson, the only two that hadn't 'slept' together. Eventually, someone farted, someone got kneed in the nuts, the tension broke, and they all relaxed. And, so it went for the next couple of days. Then on the fourth and final night of Danny's stay, they began to bicker over something. None of them could remember what afterwards, but both Ethan and he found the sight of a shirtless smug Jackson too good an opportunity to pass up and attacked.

The screeching and kicking were painful. As Jackson turned red from laughter, squirming away from the four hands running along his ribs and over his belly, they decided it was worth it. As it went on longer, there was a lull where Jackson seemed to become weak and feeble, just giving in to the tickle torture. It only lasted a few seconds before the fight was renewed.

They did feel bad about it after, but they really hadn't noticed the change from laughter to sobs until it was too late. Tears of laughter already streaked his red face, and it was hard to tell the difference. Danny realised what was happening first; wet warmth began spreading over his leg that was thrown over Jackson's hip to pull him down. Ethan's nostrils flared a second later, and his hands pulled away in an aborted movement, unable to decide what comfort to offer, they just hovered in mid-air.

The bed was wet. It was still warm. Not the weak clear liquid of a day spent hydrating well, it stank. Jackson was crying now, in humiliation. As though they had the thought at the same time, both Danny and Ethan lay down, pressing into Jackson's sides, whispering that it was alright. Danny's knee moved, pressing against the firm line of Jackson's hardness. They both gasped, and Jackson started rambling a pitiful apology about having like it. Only Danny and Ethan, they hadn't been vanilla when they were together. Both were more than happy to indulge this, especially if it meant Jackson wouldn't have something else to make himself miserable over. They nodded at each other. Danny trailed kisses down Jackson's body until he was sucking Jackson and the bitter liquid through the sodden shorts. Ethan got up onto his knees and released his own stream over the two of them, soaking them and the bed more.

In the morning, they stank, the bed reeked, and the clean up was a bitch. Danny was seen off to the airport with a long kiss from his best friend and his ex-boyfriend. They began to make plans for the next visit.

* * *

A few months later, Danny touched down at Heathrow to be met by a grinning Ethan, alone. It was a couple of days after Christmas, and Danny was staying over New Year.

Initiated by Ethan, they kissed and made their way to the underground. At Danny's questioning eyebrow raise, Ethan explained, 'you know what he's like. He wanted everything to be perfect, so he's still cleaning the flat. We'd have been later if I hadn't left him.'

An hour later they arrived to find the spare bed unmade, master bed protected with a rubber sheet, and Jackson on his third bottle of beer. Loading up, he called it. They'd all been looking forward to their reunion and planning out just how this was going to work. In the interests of not having to spend most of the week deep cleaning, most of the messier activities were going to take place in the massive shower. More of a wet room really. And thank fuck for the underfloor heating. Anything spontaneous? Well, at least they wouldn't have to throw out another mattress.

It wasn't long before clothes had been thrown off and the three men shuffled towards the bathroom in a tangle of wondering hands and kissing lips. Jackson was quickly pressed between the other two as they reached the shower, bracketed and trapped as fingers began to lightly play at his sides. It started with twitching, rubbing back into Ethan's half-hard cock that was pressed into his backside. Next came huffs of breath and embarrassing little meeps into Danny's mouth as they kissed. One of Ethan's digits traced its way down Jackson's side. The nail drawing along the underside of his iliac furrow induced the first altogether uncontrollable sounds; a series of loud snorts.

Soon enough, they had Jackson giggling, squirming, fighting half-heartedly to make his getaway. Perhaps because they were standing, or because they were deliberately moving this to the inevitable conclusion this time it seemed to take much longer. Tears were pouring down Jackson's face as he tried to suck in air in between guffaws, giggles, and sobs. His face and chest had turned bright red, and he begged for it to stop. Cruelly, his attackers continued; they'd agreed beforehand that stop didn't mean stop here.

Danny could feel the hard line of Jackson's dick pressing into his own. Pointing upwards, it meant that once again he was the first to realise that the pissing had begun. Jackson was wetting himself from their tickle torture. Like the last time, he looked utterly humiliated. Still, there was no question that it was also turning him on beyond all expectations. Jackson was grinding his cock into Danny's belly, spraying light yellow liquid, hot and steaming up between their chests.

Together they seemed to collapse to the floor, writhing and kissing. Danny and Ethan's rubbed the wetness into Jackson's skin, trailing kisses down his body. Meeting in the middle, they mixed the taste on their tongues together as their heads were showered and soaked. Eventually, the stream petered out, and the two of them stood, making out over Jackson's prone and panting form. With difficulty they aimed their straining erections down and slowly their own streams began to release. For a while, Jackson seemed content to let it splash down over him. Once he realised they were slowing down, he sprang up to his knees, grabbing them and directing the flow to fill his mouth. Letting it fill up to overflowing then swapping he drank, repeating the action three times until there was no more left.

Ethan had both the super strength and the shorter stature, so it made sense that he went first. Pressing Jackson forward to lean against the shower wall, his lubed cock began to push inside drawing moans. Ethan was thick, and it always was quite a stretch initially. It just made what was to come, seem all the more amazing. Slowly but inevitably he sank into the slick heat until Jackson's shapely ass was pressed tight against his pubic bone. Ethan began to shuffle them back, grinding himself in that little bit deeper each step and drawing out exquisite whimpers.

As Ethan leaned back against the wall, his hands hooked under Jackson's thighs, holding them back, exposing him for the next event. Danny stepped up, slicking his own dick and discarding the bottle of lube. Pressing his glans against the strained muscle of Jackson's hole, already filled with Ethan's substantial offering, he was sure that he would not fit.

'Please Danny. I can't wait any longer, I've wanted it for so long.' Who was he to deny Jackson's begging when it was so raw, real, not covering emotions with his usual swagger.

Slowly he pushed inside. For a moment he thought his cock would be crushed by the spasming muscle, but Jackson's hands came to rest on his face, pulling him into a kiss. Inch by long, well-proportioned inch, Danny slid inside until his balls hit against Ethan's. Breaking his kiss with Jackson to reach back and lick into Ethan's mouth, Danny began to thrust. As Jackson's nails scraped at his back and fingers tangled in his hair, Danny pumped his hips, his lips never losing contact. Ethan was grinding his own pelvis forward and lifting Jackson, only to drop him down to meet their thrusts. It seemed like hours, the sheer physicality of it, but minutes in, Jackson was flooded with Ethan's cum. Danny could feel it pumping through the cock he was fucking against, the tight tunnel getting slicker each time he pushed in. Jackson screamed, and sticky warmth spilt out between their bellies, in turn tipping Danny over the edge.

As they pulled out, Jackson whimpered from the ache and Ethan flipped the tap for the shower, bathing them in water, just below too hot. Clear that Jackson would not be able to support his own weight for long, they took a seat on the concrete bench on the opposite wall. Both propped him between them, as they luxuriated under the spray.

'So…' Danny began, tentatively. 'I got a job offer. It's at Cambridge.'

'Massachusetts?' Ethan asked, brain not yet up for seeing the obvious.

'No. England.' The interruption came before he even had the chance to take his next breath.

'You're taking it,' Jackson ordered, emphatic.

'But…'

'Don't care. Take it. We want you here, Danny. Both of us. We love you.'

'Oh.' Danny's beaming smile and Jackson's unaffected visage were infectious.

Ethan laughed.


	25. Day 24 - Sweat | Branding | Masturbation

**Summary for the Chapter:**

> It starts as punishment, self-flagellation, until Gus caught him. Now the sit in the sweltering heat of the forge room, Derek naked, sweat dripping down his body, as he strokes himself.

**Notes for the Chapter:**

> Sweat, Branding, Masturbation
> 
> Temporary and permanent marking from branding. May be considered self-harm. Skip if you aren't sure.

It started as a punishment, self-flagellation until Gus caught him.

When Laura had told Derek they were leaving for New York, he's assumed that meant the city. Instead, they found themselves in some crappy little town in crappy dead-end jobs. For more than two years Derek didn't do anything fun, didn't laugh, didn't enjoy. Then the farmer he was working for at the time took him to get the horses shod. It was a one-man deal—a traditional blacksmith. The owner was called Gus. He was in his forties, thickly muscled, a bit overweight, and Derek was fascinated. With the man, and the heat and fire that spilt from the forge. With the red hot steel. Luckily he was a natural and Gus needed some help.

Now they sit together in the sweltering heat of the forge room, Derek naked perched on an anvil, sweat dripping down his body as he strokes himself. A leather strap clamped between his teeth. Every few minutes, sometimes ten, sometimes thirty, Gus stands and pulls another brand out of the fire. Each time he presses it to a new piece of Derek's flesh then sits back down and starts to edge himself again.

The longer he worked there, the more Derek was trusted by Gus. It means that when the man caught him, pressing a poker to his exposed arm, a flood of shame joined the humiliating from being busted like this doing something so bizarre. If he'd been normal perhaps he could have passed it off as something else—just a typical broken teenager, or maybe an accident. The tented wet spot in Derek's jeans was what drew Gus' gaze.

They've never touched each other. Gus never asks what Derek is.

Dropping the poker in shock at being caught, it didn't occur to Derek he was revealing a bigger, more dangerous secret. It wasn't until Gus' eyes moved away from his crotch, that Derek felt the flesh knitting back together and he ran. Unable to stay away, fear of the unknown too great, he returned the next day. Put to work like usual it was confusing until at the end of his shift Gus sat him down and explained that if he wanted to use the smith to hurt like that, the rules needed to change.

The day before Derek returned to Beacon Hills, Gus asks if he wants one to keep. Derek wished he could.

Laura wouldn't tell him anything, just that she was going back, she didn't want him to worry. He was terrified. Then she stopped calling. His insides felt hollowed out. Beacon Hills was beckoning to him, and there was nothing to anchor him.

It was different the final time, made to bend over the anvil, pretty sure which part will be branded.

It's better and worse, and it's the first time Derek's cried or felt the leather really necessary. The mottled skin is raw and painful to touch.

There's an old dirt-coated floor mirror that a customer never picked up. Burned into his skin, a permanent reminder. An omega.

Gus was gone. The forge was cold; it looked like it hadn't fired in years. Next to the brand was a jar, filled with rowan ash that Derek shouldn't touch. They had a contact halfway between here and California, with a blowtorch and a tattoo gun. There were ways to burn marks into his skin he now knew. Picking up the bottle, and the Ω brand as an afterthought, he went home, packed, and began his journey. Home.


	26. Day 25 - Bondage | Gunplay | Inflation

**Summary for the Chapter:**

> The benefit of being a werewolf with an extreme kink is how much further you can take it. Derek is strapped to a chair made of mountain ash. Slowly he's filled to bursting. Belly swollen and distended from overfilled bowels and bladder. The he's kissing and licking the barrel of a revolver before it's forced into his mouth.

**Notes for the Chapter:**

> Bondage, Gunplay, Inflation, GSW, Wounding, Pain, Extreme Edge Play, Object Insertion, Bowel Inflation, Enema, Bladder Inflation, Ball Inflation, CBT
> 
> WARNING: Given the combination of prompts for this day and the healing abilities of werewolves, I went extreme on this one. Includes gun play with gun shot wounds, and other things that wouldn't be safe for humans. Beyond graphic wounding, this may also be considered body horror by some. Proceed with caution where applicable.

Stiles was into some...questionable shit. He was pretty sure none of it was actually illegal. As long as it stayed in the realms of fantasy. Then Derek came along. Derek, the werewolf. Derek who could heal from pretty much anything. Derek who was as equally fucked up as Stiles.

The benefit of being a werewolf with a set of extreme kinks, was how much further you could take it. Having a human boyfriend how loves to see you suffer just makes it pop all the more. Literally. Strapped to a chair that had been specially built for this purpose, the benefit of being a wealthy werewolf with a set of extreme kinks, Derek prepared himself for what was to come. It promised to be spectacularly horrific. For him, at least. Possibly anyone unlucky enough to stumble upon the scene.

The seat of the chair had a broad plug in the base that was a painful stretch, even with the oily lube that as well as easing entry would serve as an extra leak guard. Through the centre of the plug was a hole, half an inch wide, with a hose screwed into the base.

Pushed deep inside his flaccid penis is a rubber catheter snaking down his urethra and prostate, and into his bladder. If that were all, as unpleasant as most men would find it, it wouldn't be so bad. The one-way valve on this device was backwards, letting a stream with enough pressure in, and nothing out. It was held in place securely by a clamp that was part of the chair's design and built into the front of the seat—a hose connected to the other end of the tube.

Between the plug and the catheter clamp, was a hole in the seat of the chair which was just big enough for Derek's large and low hanging testicles to fit through. They dangled in the air, a needle pushed into the sack, thankfully connected to a drip this time, rather than a hose. Soon enough it would be the least of his worries regardless.

'Ready?' Stiles asked, grinning, looking positively evil.

'Please,' Derek groaned in response. 'I feel so empty.'

The drip was turned on first, and for half an hour, Derek was left to feel the weight pulling his sack down as it grew more massive with fluid. The whole thing was being filmed for their later enjoyment, but for now, he had to imagine. It had probably been inflated to twice its regular size when Stiles came back, carrying a hard-shelled case.

Next was the hose attached to the plug. It was connected directly to the cold main. The cold water added to the experience brought the cramps on faster and more unpleasantly stimulating. Derek revelled in the torture. It was only a trickle really, slowly filling him up. Still, his dick was already firming painfully around the rubber tube stuffed inside it. For another hour, Stiles left him to grow, inflating his bowels with icy water. A human would have probably gone into shock, either from the pain or the cold. Derek just whimpered and sweated it out. Chin against his chest Derek watched as his belly began to push out, muscles stretching until all definition disappeared in a distended beachball filled with water.

Perhaps the most painful part before the finale, Stiles returned once more and turned on the catheter pump, sending liquid the wrong way to stretch and expand Derek's bladder. Before Stiles, it would have never occurred to him that there was yet something else he could blow up and swell to breaking point.

It's not long before it goes beyond the point even the most extremophile would consider pleasurable. With swollen ball sack hanging down the occasional movement scraping it against the concrete floor and bladder fuller than holding too long achieves, that's when the tears start. His insides are still expanding, beginning to crush vital things, but Derek wants to be blown up as big as they can get him.

Once, despite their precautions, water started to leak from all three areas, Stiles shouts off the flows and opens up the case to reveal a .45 revolver. Last time they tried a 9mm, but it was underwhelming, so they decided to go all out. The bullets, waiting to be fed into the chamber are all the regular kind. Sort of. Not wolfbane, but long colts. Half the fun of having a balloon is watching it pop.

Stiles pushed the barrel into Derek's mouth, not bothering to work up to in, just thrusting in and out while he fellated it; made it sloppy.

The gun left his mouth, and Derek moaned as the hammer cocked next to his ear, whined when the trigger clicked a second later while the barrel pressed into his temple. Even for a werewolf, with a gun of that calibre, that could be considered a stupid thing to allow. Still, he trusted Stiles to only hurt him in the rights ways. 'Please Stiles,' Derek begged. 'My belly hurts too much.'

When Derek opened his eyes again, Stiles was over at the table, slowly loading the bullets into the revolver's chamber. The Beretta Laramie had six chambers and Derek had no idea which ones would be blanks. Unless by sleight of hand, neither would Stiles once he'd rotated the cylinder. Moving in front of his target Stiles adjusted his stance for the powerful weapon and aimed.

Bang! The first shot was loud but only a blank. Regardless, the anticipation shot through Derek, setting his nerves on fire. Bang! At the second blank going off, his orgasm began to build. It would rip through him with a fury and nowhere to go. Bang! Derek came. His insides seized as his load futilely forced its way around the fluid-filled catheter, feebly oozing around the rubber at the raw tip of his slit.

Tears were pouring down his face now. His insides were inflated to push his belly out to the size of a man three times his weight. Without the burning horniness to maintain him, it became pure torment. Bang! A ripple of flesh then searing agony. Red water, like wine, began to spray from his middle, halfway between his navel and sternum like someone had tapped a barrel and left it running. Slowly the burst balloon of his midriff began to deflate. Even as the pressure kept the round wound open Derek felt torn organs start to knit themselves back together.

Bang! Derek's eyes shot up in surprise, another blank, but that meant Stiles was expecting another bullet and the aim was no longer at his centre. Stiles' smile was cold and distant as the barrel of the gun pointed down, underneath the chair. Derek struggles against the restraints, growled, began to shift, even as he began to stiffen again over the tube inside him. 'Don't you dare!' His growl was ignored.

Bang! The pain was exquisite as he felt the explosion of warm fluid against the back of his calves and coating his naked feet. Nothing like that had ever happened, never had he been injured there so badly, and he wasn't even sure if it would heal like the rest.

Stiles waited. The water and blood continued to leak out, getting slowed. Derek's face has shifted, his eyes were glowing, and claws scraped at the rowan wood arms of the chair. When the weight had reduced enough, and the pressure plate clicked Stiles' smile widened. He had lost his chance to run. Derek jumped up, screaming as the plug pulled out of his hole and his tattered sack was yanked violently through the barely large enough gap in the seat. Stiles began laughing but only backed up slowly. Derek ripped out the catheter with clawed fingers roaring again before he pounced.

Faster than he could process, Stiles found himself thrown over Derek's shoulder, his jeans shredded by careless swipes. The gun was ripped out of his hand, and the five inches of still-warm barrel shoved inside him took his breath away. Batting and scratching, Stiles fought against Derek, marking up his back only for it to heal instantly. Then relief as the barrel was withdrawn; a short-lived reprieve. The grip was forced inside, and Derek began to bugger him with it, mercilessly. With a curve down, the angle of the grip meant every hard movement jabbed it relentlessly against his prostate, over and over it hit as Stiles ground his hips into Derek's shoulder. Even after he came, Derek continued until his wrist was sore and the sobbing was leaving a wet trail of tears and snot down his back.

With his passenger still hiked over his shoulder, revolver grip buried in place, Derek set off in search of the bicycle pump and hemp rope. He might not be able to use a loaded gun, but they were still going to play with it when Stiles discovered what it felt like to have his insides inflated beyond belief.


	27. Day 26 - Stripping | Scat | Burnplay

**Summary for the Chapter:**

> Weird sex club for supers. Derek and Parrish strip, a special show for a high flyer, they always get the freaks cause they are and they never say no. Derek lays back as Parrish hikes up his legs and licks into him pushing down on his belly as he starts to run his hands over Derek's thighs, smell of burning flesh and hair in the air, his bowels release.

**Notes for the Chapter:**

> Stripping, Scat, Burnplay, Eating, Feeding, Smearing, Cigars, Cigar Burns, Sex Work, Hooker Husbands
> 
> WARNING: Today's prompt included scat and burning so this chapter does too. If you don't like shit and you don't like burns, skip this chapter.
> 
> Otherwise enjoy you dirty perverts ;P

Hale and Parrish worked at one of the west coast's more unusual establishments. The rules of 'Second Circle' were simple. Nothing was off-limits if the talent agreed to it in advance. The private club is known colloquially as 'Lust' by those in the know, catered primarily to supernaturals and supernatural adjacent normies. And the duo of Hale and Parrish had a well-developed reputation for taking on the weirder client requests.

Today's booking was a doozie. Luckily Derek delighted in feeling pain, and both of them would play in filth like pigs in muck. They always got the freaks because that's what they are. And they never say no.

The stench of wolfsbane hung in the room with the thick cigar smoke when they entered. Servicing hunters always made Derek's dick twitch. The guy, Argent, wanted a show first, slow and sultry stripping. The pair began to gyrate to the music as they crossed the room, grinding together and divesting each other of their shirts.

Derek bent over in front of Argent, hands on the floor and ass almost it the guys face. Jordan squeezed his hands under the tight waistband of Derek's shorts, pushing them slowly over his thick ass cheeks. Quickly their client got with the program, taking over and exposing the jockstrap framed cheeks and the stink of dirty hole so close to his face. Everything about this was choreographed down to the clothes. But once it got physical and passions flared, the pair's propensity for going as far as the client wanted in the moment was what had them rolling the four-figure tips.

Stepping out of the discarded shorts, Derek began to roll his hips and shake his ass. Showing off its impressive jiggle before losing himself in a raunchy lap dance to heat things up, he didn't hold back. Parrish wasn't idle either. Argent's eyes were locked on him as he continued his striptease with his trademark move. The faster he danced, the more his clothes began to smoke until the hell hound burst into flame, glorious and naked. Lighting a fresh cigar for Argent with his tongue seemed to get the clients attention as his hands began to explore Derek's body.

Together they pulled Argent up and over to a chaise that was better suited for their plans. Sat back against the arm, legs spread, Argent puffed his cigar and watched his toys for the night. Parrish was smooth, lithe, and hairless, covered now in a patchwork of black smudges; carbon from his immolated clothes. Now he was naked, everything had burned. There was a slight swell to his otherwise flat muscled belly promising a long entertaining evening. Derek was thicker and hairy and looked like it would be impossible for him to pretend to be anything other than filthy. Per Argent's request, Derek was tucked away in a jock, the pouch of which was nicely filled. His belly looked even fuller. It was time to start.

'Strip me,' Argent ordered. 'And call me Chris.'

The pair moved in together. Parrish knelt to remove Chris's boots and socks while Derek started from the top. Taking the cigar and puffing on it himself with a wink, Derek pulled off the T-shirt. He admired the surprisingly well-muscled frame of the older man before blowing cigar smoke in his face and handing the stogie back. He took his place then, on his back in between Chris' legs, head resting against his lap.

Jordan didn't waste any time then, pushing Derek's legs back and telling him to hold them. Knees pressed down into the couch, arms hooked around his calves, Derek was bent in half and exposed. His own hole was in view, making him throb in his jock pouch and the sight of Jordan sniffing at his fetid crack made him moan.

A tongue swiped over his hole, flat and rough and heat began to radiate through his ass cheeks until it started to sting. The smell of burning hair filled the room, tangling with the thick cigar smoke. Jordan's tongue speared into his hole as the first burning smack to his cheeks made him whimper. It blistered and healed before the hellhound planted another, harder, hotter, more painful.

Jordan's tongue dug deep until it hit firm resistance and bitter taste flooded his mouth. Pulling back with a grin, he began to lick and suck at the rim, moving his hand to push down on Derek's bloated stomach. A groan of pain turned to a moan of relief as a trickle of gas forced its way out followed by a further eruption of vile air. All three of them breathed the stench in deep, filling their lungs with rotten eggs, burnt sulphur, and thick cigar smoke.

As the pressure on his belly grew with the hand pressing in harder, something shifted inside him, and Derek gasped. Slowly the built up store of crap began to force its way out. Fascinated he watched as the first semi-firm log grew upwards before a nudge from Jordan's nose sent it tumbling to Derek's belly. Lips closed over his now soiled cunt, and the hands on his abdomen began to massage more firmly even as they spread around the stinking waste that had fallen. More shit began to force its way out, straight into Jordan's waiting and hungry mouth. The air was starting to mix in the newest foulest smell.

Some Jordan swallowed after chewing and making it into a thick, nutty, bitter paste. Still, most of the scat was allowed to dribble out mixed with his saliva. The wetted combination made it easier to spread over his own face and body as well as coating Derek's lower half mating down his dark hair with brown. When they did this, it always thrilled him, destroying the clean-cut vanilla image he presented. The fetid feast made his stomach churn with unpleasant spasms, but the sheer depravity of it made him too turned on to care. It never came back up. At least not unless the client wanted it to.

Derek was lost in his sick little world getting hit from the mix of scents that would make most humans hurl, let alone werewolves with their super-sensitive noses. He'd always known he was built differently. Dripping into his now shit caked jockstrap and revelling in the feeling of feeding Jordan whose tongue was digging deep in his ass distracted him. Derek wasn't prepared for Argent's next move. What started as a pained whine grew louder and then morphed into a roar as he shifted, digging claws into the couch. Chris's cigar had been pressed down hard onto his left nipple. Just as it was taken away and the burnt flesh began to heal the smouldering foot of the cigar landed on his right.

As Derek cried, Jordan's time at his shit dispenser had come to an end, Derek's bowls emptied and his belly flat once again. 'Come up here and let me taste,' Chris said. 'I want to watch you fuck him while I lick his mess off your face.'

Who was Jordan to say no to that? In a forty-five degree plank, he supported himself with his weight on the arm of the chaise and his dick rock hard and ready pressing against the shitty hole. Slowly he allowed his hips to fall and his cock to sink into the wonderfully slick cunt. There was nothing better than a shit fuck. As gravity continued to do its job down below his head dropped, tongue ramming into Chris' mouth. It always got him going, sharing this part of Derek. Chris was eager to taste it, his own tongue swirling with Jordan's, slipping out to lick the stinking mess from his face, brown slobber renewing the foul face mask.

Without even realising it, Jordan's hips had started to lift and fall, pulling up slowly and driving back in as fast as gravity would allow. The pounding was drawing little growls and whimpers from Derek; always a needy greedy bottom. Fucking faster and making out with the shit hungry client was bringing Jordan quickly towards a powerful and violent orgasm. It was another thing on Chris's wish list but not something they could promise, so it seemed they were in for a big tip. Jordan's knot began to form, and with the angle and his weight, it only took a handful of brutal drops against the battered hole for it to lock inside. The heat began to build and pulling it away from his face still pressed into Chris, meant fixing the coming meltdown lower, focusing on Derek.

Roaring into Chris's mouth, Jordan began to cum, filling Derek with searing hot liquid which made him start to sweat profusely. The pumping would go on for hours, causing Derek's belly to swell with baby batter. After they rested and the knot deflated, they all would feast on it as he shat it back out. Jordan's lower half was still on fire, burning Derek's ass, and red hot hands seared the backs of his thighs. There was only one thing better than his husband's knot and flaming touch. Later Chris and Jordan would switch places, Derek would feast from Jordan's ass while the Hunter fucked him. They'd change again, Derek still the toilet. Then Chris would leave. The couple would fall asleep with Jordan's knot back inside him, pumping him full once again.


	28. Day 27 - Public Sex | Role Reversal | Xenophilia

**Summary for the Chapter:**

> Derek should have listened to Laura but kid she used to babysit was weird. Not to mention hot. Now Derek was pressed against the window of his mom's office as he looked through the gaps in the blinds. Anyone could come over and peer in, or burst through the door. They’d see him with his pants down around his ankles, a decidedly not human tongue pressing inside him.

**Notes for the Chapter:**

> Public Sex, Role Reversal, Xenophilia, Full-Shift (think Peter/traditional werewolf rather than a wolf), Knotting, Breeding, Werewolf Stiles

It was definitely an 'I told you so' moment. Derek should have listened to Laura. She'd always said that the kid she used to babysit was weird. Since the gangly baby giraffe-like blabbermouth had returned to Beacon Hills, mysterious and significantly grown-up he seemed more abnormal; not to mention smoking hot. Derek may have become slightly obsessed. Of course, he hadn't listened.

Now Derek was pressed into the window of his mother's office, looking through the gaps in the blinds. The deputies were going about their work in the squad room, unaware. It was a pretty good bet they'd get an eyeful of his slack-jawed drooling face if they walked over and peered in. If any burst through the unlocked door, a picture of Derek, pants around his ankles, would have greeted them. A decidedly not human tongue poking inside him covering him in slobber would undoubtedly have proven a shock.

Derek was not...worldly. Okay, he was a twenty-two-year-old virgin about to get railed for the first time by a monster in his mom's office with a very high chance of getting caught. It made him harder than any fantasy ever had. After your teenage sweetheart gets mauled to death in the woods by some animal, you tend to find the desire for relationships wanes. And Derek wasn't really one of those boys who had any desire to sleep around, less so after Paige. Of course, the next person even trying to get into his pants being a creepy, bad-touch substitute teacher was just the icing on the cake. In so many different ways, especially with her bizarre werewolf obsession.

Chance had brought Derek to the station today, dropping off a file to the cute deputy, Jordan. Derek was pretty sure his mother was trying to set them up but didn't want to come out and say it to their faces in case it made things awkward for her employee. Only, as much as Derek liked Parrish, there was something else which took up most of his attention. And, that something, had just broken into the Sheriff's office. Derek's mother's office. Being in a room full of policemen really should have clued him in to the proper course of action. Still, whether through his Stiles shaped blind spot or some notion about protecting his mother's integrity, Derek snuck in after, closing the door behind him.

Stiles was rifling through one of the filing cabinets when Derek asked, 'what the hell do you think you're doing in here?'

'Looking,' came the nonchalant reply. Stiles held up a file over his shoulder and waved it in an indication Derek should take it. Unsure why he did. Stiles kept rummaging.

A sigh. 'For what?'

'Nunya.'

'Mature. I work in here during seasonal breaks doing filing. If I knew what you were looking for, I could either tell you where to find it before you get caught or tell you to fuck off before I call someone in here. Depending on what it is.'

Stiles turned around, a smirk on his face, and leaned back against the cabinet. 'Now why would goody-two-shoes Hale be offering to help a little reprobate like me?'

Derek choked on the reply that was forming when a tongue flicked out, and nostrils flared. 'I..I...' he stammered. Stiles grin just grew broader, more toothy.

'I make you nervous, don't I?' Stiles asked the question with a barked laugh as though just realising. 'Little old me? One hundred and forty-seven pounds of pale skin and fragile bone. Sarcasm is my only defence. What could I possibly do to make you nervous?'

Gulping Derek replied, playing for time. 'One forty-seven? You're at least one sixty. You...put on a lot of muscle since high school.'

The grin was hungry now, Stiles' eyes had narrowed like they'd just spotted a weakness. 'Noticed that did you? Paying a lot of attention to me, Derek?' Slowly he sauntered over. They were the same height, in fact, Stiles may have been a hair taller. There faces only inches apart Stiles breathed out again, 'why do I make you nervous, Derek?'

His mouth had gone dry, and Derek could feel himself beginning to stiffen in his jeans. Something made him want to bend over and submit, but that would be beyond embarrassing to admit. 'There's something off about you. Sneaking around, being places you shouldn't. You're up to something, and it makes me worry.' Right enough, unless...

'Liar.' Stiles' nostrils flared again. 'That might all be true, but I asked why I made you nervous, and I think it's because you like me, Derek. I think you like me a lot.'

'I don't...' he began, but the lie was cut off.

'You do Derek. Would it help if I told you I like you too?' Stiles' hand moved to cup Derek through his jeans, and he whimpered in response. 'Tell me I'm, wrong. Tell me to stop, and I will. I'll not come near you again. Tell me you want it, though. Let me hear you beg, and I'll take you apart right here. I'll show you all my secrets and make you mine. Would you like that, Derek? For me to be your first. Your only?'

How he knew exactly what was being offered even though all rational thought disagreed Derek might never know, but he did. It was a question for another day, but what had been proffered there and then he wanted, entirely and unconditionally. 'Please.' He whispered.

Stiles pushed him back until he was pressed against the windowed wall, lucking the blinds had been mostly closed. The kiss surprised him, soft and tender, but it quickly turned harsh and claiming. Both, for different reasons, made his heart beat faster. Pulling back and taking a few steps away, Stiles began to strip out of his clothing, and the view was incredible.

'So,' a gloriously naked Stiles said. 'I'm going to claim you today, and while I think deep down you know what that means... don't scream, okay?'

Derek nodded both understanding and not at the same time. It was like a part of him knew, but another part was fighting to keep a bursting door closed. Then the horses bolted. In front of his eyes, Stiles' bones began to rearrange. First eyebrows seemed to vanish as hair sprouted from the sides of his face and teeth began to elongate. Then his face began to stretch. Not hair, not teeth, but fur and fangs, grew on the elongating muzzle. The rest of Stiles' body was changing too. Growing taller and thicker and considerably more hirsute, eyes glowing red a monster now stood in his place. Derek couldn't tear his eyes away from what was happening downstairs, though. Stiles balls seemed to darken and swell much larger while his dick seemed to shrink away. Then Derek realised it wasn't shrinking, rather changing, a sheath covering all but the bright red pointed tip.

The beast stalked forward eyes burning crimson, it's snout pushing into Derek's neck, his armpits, bending to sniff at his crotch. When a long wet tongue began to lick his face, all he could do was drop his mouth open, gasping as the long appendage licked inside. Then he found himself flipped around, sharp claws scratching at his belt buckle. Both to speed things along, and because he didn't really want those things getting impatient in that area, Derek unbuckled, unbuttoned, and pushed his jeans down. They slipped over the swell of his ass, underwear in tow, causing his dick to slap out against the wall.

When the tongue trailed lower down his back, Derek began to shake with anticipation. As razor-sharp nails carefully pulled apart his cheeks, he keened with need. When the long floppy tongue scraped over his hole, then firmed and pushed inside Derek let out a sob. Only his fingers had ever explored that part of him, and they'd never gone so deep, never felt so hot or wet. Hot moist breath panted out over his lower back. He began to rock back into the probing muscle, feeling the prick of the fangs that big muzzle held, as it occurred to him his first time was getting fucked by a werewolf.

Daring to twist and look back, the urge to pet the beast took him and without thinking it through his hand began to scratch behind one of Stiles' pointed ears. A fully shifted werewolf purring with its tongue jabbed against your prostate was quite the experience, and Derek jerked, knocking his head against the blinds. It did occur to him to check if anyone noticed. Craning around a bit further he could see down to where the magnificent length of flesh poked from the sheath no longer looking remotely human if anything it was…canine.

Apparently bored of his meal Stiles pulled back his tongue and stood, towering over Derek's face. For a moment he stared, seemingly hesitant. Something in Derek's eyes must have spurred him on as the tongue began to lick into his mouth again. Then the poking started. It only took a couple of uncomfortable jabs before Stiles found his mark, and Derek's breath was snatched away. Slowly, oh so slowly the huge beastly cock pushed its way inside him. It was concurrently as though he was being torn in two, and the best thing he'd ever experienced, the deeper it sank, the greater both feelings became. Derek's breath had been taken away and only returned when he felt Stiles' hairy hips come to rest against his lower back.

Slowly Stiles began to grind his cock without thrusting. It wasn't until Derek started to rock his own hips back that the thrusting began; first slow then gradually building to a pounding beat. Each out stroke left him feeling incredibly empty, and each hammer blows back in pounded against his prostate. Untouched, his own cock was stiff and leaking and ready to blow.

'Mine,' the grating growl sounded hot in Derek's ear sounding as though it was forced through a mouth that wasn't made for talking. 'Say you're mine, Derek. Tell me you want this.'

'I'm yours, Stiles, always been yours. Waited for you even though I didn't know why,' Derek panted. It was true. For some reason, he'd been saving himself for this. 'Make me yours.'

A pressure built against Derek's hole as something larger began to knock against his rim. It popped in just as he realised what it was, a knot. They were tied together now, and the tennis ball-sized lump was crushed against his prostate. Derek looked up. Where he'd knocked the blinds earlier, there was now a more substantial gap. Across the squad room, Jordan stared straight back, a grin on his face. Jaws clamped down on the back of his neck as a flood of warmth spread through him.

Derek came. His cum shot out against the wall. And, as he began to blackout, he wondered what exactly had tipped him over the edge; or if it was just the explosion of too many sensations.

It wasn't long before Derek awoke again, the feeling of a hot tongue licking over the side of his face. Turning slightly, it found his mouth, and he ducked on the muscle as he peered back out through the window. Deputy Parrish was still staring right at him, and then to his surprise, the man's eyes flashed a flaming orange. The shock made him gasp then the tug against his hole made him gasp again. The deflating knot popped out only to be replaced by probing, and very human, fingers.

'I think Parrish knows, it looked like he was watching and his eyes flashed,' Derek croaked. It seemed significant, but for the life of him, he couldn't fathom why.

'Took me so well,' Stiles wondered. 'Like you're made for this. Made for me. Mate.'

The title made Derek shiver with longing. 'Mate.' He repeated. A confirmation, not a question. 'But what about…'

'Shh,' Stiles interrupted, tilting his head, resting it on Derek's shoulder. 'Oh, that's perfect. The dirty little hound got off on watching your first time, baby. Wants to join in next time. Should we let him? He says such filthy things.'

Derek peeped back out through the window, and sure enough, Parrish was still staring in their direction, lips moving like he was talking to them. 'I thought you said I was yours. Only yours?'

'Oh, you are, baby. But I had an excellent babysitter who taught me to share my toys.'

'Oh fuck,' Derek whimpered. Imagining Stiles and Parrish both sliding into him together, wondering what the deputy turned into, he hissed, 'please.'

'This will be so much fun, babe. I'm going to be such a good Alpha for you. Providing for my mate. Keeping you wet and dripping and sated. You're going to be my perfect slutty bitch and keep my new pack so happy.

It was enough to push Derek over the edge again, a second load feebly shooting out against the wall. Then his mother entered the squad room. Parrish successfully waylaid her but not before mouthing something else in their direction.

As they scrambled to get dressed, clean up, and clear out without getting caught, Derek's curiosity got the better of him. 'What did he say?'

Stiles laughed. 'You're going to be paying for that save for a long time.' At Derek's somewhat edgy looks he added, 'oh don't worry, I have every confidence you're more than capable of taking us both. One at a time at least.'

Sneaking out of the office then to the door at the back of the station, Derek sighed as he felt himself beginning to firm up in his pants once more.


	29. Day 28 - Crossdressing | Lingerie | Distention

**Summary for the Chapter:**

> Derek can’t believe that he’s doing this but every time he passes some random person and they tell him how hot he is the bulge in his dress gets more obvious. This is new to him, the next part is what he’s good at. Taking fists 'till his belly bulges.

**Notes for the Chapter:**

> Crossdressing, Lingerie, Distention, Fisting, Corsets, Public Sex, Sex Show, Belly Bulges

Derek couldn't believe he was doing this, but every time he passed some random person who'd stop him and compliment him, he preened. Each time it happened, each time someone told him how hot he was, his bulge would grow a bit, becoming more evident as it stretched out the front of his tight black dress.

This was new to him, all of it. Well, what was coming next he was an old hand at, but meandering through the club, in three-inch stilettos and a cocktail dress, that was new. It had always fascinated him, watching other performers all dolled up. But until the latest crew had arrived with their incredibly terrifying wardrobe manager, Lydia, he never would have dared to indulge.

For the last couple of months, he'd been spending his evenings at her apartment, sometimes just the two of them, sometimes with the peanut gallery as a raucous audience. She'd started him on smaller wider heels, progressing as she praised his natural abilities. It was exciting, but then she told him to arrive in tight pants instead of his usual off duty jeans the following day.

That night a pair of two-inch stilettos awaited him. They were pretty, but he wasn't really sure how this would make him fall in love with crossdressing. At least until Lydia had him sashay over to the full-length mirrors taking up two corners of the room. He looked terrific in the tight jogging pants but…

'Can I…?'

'I insist, even if I'm not going to touch I can still enjoy the show,' Lydia replied, sipping her wine while sitting on her rattan throne. She knew exactly what he needed.

Squatting in the heels, Derek unzipped the bottom of his pants legs then removed them without bothering to take the shoes off. Now stood in a pair of tight briefs He marvelled at his assets. The pointed-toe T-straps made his calves strain, and his already enormous behind seemed to stick out even further. Excitedly he turned to his mentor and demanded, 'more! Though...what do you think about all the hair?'

* * *

Two months later he was wandering through the throng of sweaty bodies, meeting people, waiting for his turn on the stage. Thigh-high white socks were held up by a lacy garter belt, and white lace panties barely contained his less feminine parts. It didn't take much to catch a glimpse, the skirt of the dress was short, and only the considerable swell of his ass held the thing down, stopping it riding up. It also had the secondary effect of pulling the front tighter against his crotch. That was making it very clear to everyone quite how much he was enjoying being dressed up like this in public. Lydia had slicked his hair back in a Jamie Lee Curtis, 'True Lies' manner and applied his makeup. The dark eyeshadow and cherry lipstick seemed to suit him. She had insisted that his body hair and trimmed beard, or at least stubble, remained. Nothing they did was ever going to make his shoulders narrow or round his cheeks, so why not accept it and blend the two together.

What they could do was to cinch in his waist. Lydia, despite her diminutive stature, was ruthless when it came to lacing corsets as her on-again-off-again boyfriend Jackson, and now Derek could attest. It squeezed his waist in nicely, framed his pecs beautifully, and made his best asset...his ass, really stand out. It would look great on stage when the dress came off, and things started to heat up as well. His call to prepare came, and Derek went backstage to see his co-stars.

Liam, Stiles, and Theo all wolf-whistled as Derek joined them, it was the first time they'd seen him with a Lydia wardrobe special. They were all in jocks, boots, and leather harnesses. This was his turn as the star of the show. Lydia had insisted the focus wouldn't be taken away from the explosive finale.

'Ready?' Theo asked.

Derek snorted. 'Apart from the clothes, I'm an expert. I could do this in my sleep.'

'You did that last week,' Liam laughed. 'Didn't even wake up once.'

'What can I say, I'm a bottomless pit with an insatiable appetite.'

The three boys made their way out on stage to whoops and cheers and began their routine. Derek waited nervously for his cue. The only thing keeping him from bolting was the knowledge that soon there would be no room left for the butterflies that had taken up residence in his belly.

His song played, and Derek put on his mask; confident he sashayed out onto the stage with the catwalk run he'd perfected with Lydia. Liam and Stiles were waiting for him, to grab him, spin him, and tear off the black dress leaving him in the corset and lace underwear. The panties wouldn't last long. As he folded himself in half, head between his legs and hands around his ankles, the pair began to slowly peel the lace away, licking and kissing the exposed skin as they went. Then came the preparation. Greased fingers and toys started to work open his hole. Theo appeared in front of Derek, standing on a chair. When he felt he'd been sufficiently opened, Derek stood back up shaking a kiss with Liam and Stiles then widened his stance and leant against it.

Theo began to run his fingers through Derek's hair. He pressed the open panting lips into his hardness, straining the pouch of his jock. For his part, Derek mouthed at the package eagerly waiting for it to be unwrapped and fed down his throat. There wasn't long to wait. As one of the boys behind him forced the widest part of their hand inside, Derek gasped, and Theo grasped the opportunity to slip his cock into the talented mouth. The fist inside Derek's ass pushed further, and when elbow hit his rim, he could tell from the depth that it was Liam filling him. Stiles had longer forearms.

Over and over the arm filled him and emptied him, leaving him gaping as it pulled out to apply more lube. At some point, Stiles had taken over. Still, Derek just maintained his blissful drifting, full at both ends, on stage exposed to hundreds of people and their cameras.

Instead of withdrawing per the pattern, an arm sank deep, remaining as the second began to push in alongside. Now the challenge commenced. Derek could feel his insides rearranging to welcome the intruders just like they had a thousand times before. The tightness of the corset was adding a new exquisite sensation. Where his usually flat and muscled belly would bulge from the arms inside him, only a small ripple could be seen. The tightness of the corset was keeping the pressure on and everything in place. Though, he could feel its seams begin to strain. Lydia had adjusted this one especially. It would fail under stress, the question was how wide and deep he would have to be stretched first.

Both arms were inside to the elbow when the corset finally gave way, the side seams popping open and the loss of the pressure had Derek's gut suddenly realising. The vision of arms moving inside and making the skin of his belly stretch out as they moved proved too much for Theo's sense of control. Quickly he pulled out of Derek's mouth and with two strokes, blew his load in his face. It was time for a change in furniture. Derek was laid down on the floor, and this time Theo took his place at the voracious hole. After greasing up, he slid straight into the elbow with no resistance at all. Derek was still wide open from the other pair's joint excavation. Having a little fun, Theo began pressing his fist upwards, watching as it raised a lump of distended flesh on Derek's belly. The whooping from the audience suggested they also approved. It was his job to get depth though so he began to slowly sink in deeper.

As Theo got to work, Liam and Stiles each took one of Derek's thickly muscled arms and liberally coated them in Crisco. It was their turn to be impaled. Derek wasn't really in any position to do the work in his fucked out and delirious state. So, they planted his upper arms flat on the stage perpendicular to his body and his forearms straight up at ninety degrees. It meant that when they took their seats, they hand a stable base to bear down against as they tried to force Derek's balled fists inside their holes. No one was as experienced at this as Derek, but Liam and Stiles had still had more arms inside then than most people had hot dinners. Liam was first to relax enough for the broad hand to pop inside. Gravity took him down a few inches off forearm before he could arrest his fall, making him cry out in overstimulated ecstasy. Never one to be outdone, Stiles rose up then dropped down hard. The fist punched through his rim, and if there was one thing that came naturally to him, it was taking it deep. Sinking down, not trying to stop himself, Stiles ended up with one of his asscheeks resting on Derek's bicep as he landed his hands behind him. Slowly he began to lift and drop, and Liam was now mirroring him on the other arm.

Theo looked up at Derek's belly as his arm slipped in the last couple of inches to bringing his armpit in contact with the stretched out rim. Derek was breathing hard, his chest sweaty and the movement of the arm inside him clearly visible from the outside. Theo's gaze went further to watch the other two who were making their own contribution to the art of distended bellies. Riding Derek's large arms was pressing out bulges just above their navels. Both were beautiful but Stiles, with his slighter runners figure, showed the shape more clearly. Theo's could swear the gaps between Derek's fingers were visible.

They were getting exhausted, and it was nearly time for the finale. Liam and Stiles fished their dicks out of the pouches of their jocks and began to stroke themselves, aiming at Derek's chest and holding out until they made him cum first.

Using his mouth on full to burning bull balls and his free hand to stoke Derek's hard and weeping cock, Theo got to work. It wouldn't take much, but for a little added alacrity, he started to talk. 'That's it Der, such a good girl, taking me so well, pretty cunt stretched open wide taking me deep. You looked so hot in your dress. When we get home, we should throw out all those nasty jeans, boots, and boxer briefs. From now on, it's pencil-skirts, stilettos, and pretty lace panties, babe. What do you think?'

With a roar Derek came, splattering his stomach, pecs, and even Stiles, Liam, and his own chin. The arm riding pair was soon to follow him over the edge, hitting each other and his chest with big loads. It took them a few minutes to get their bearings, empty their holes, and gingerly make their way off stage. They'd be doing this act again. And, when they got home, three exhausted men were going to go to town on Theo's ass. He wasn't getting off that lightly when they could barely walk.


	30. Day 29 - Praise Kink | Glory Hole | Telepathic Bonds

**Summary for the Chapter:**

> Derek is controlled by Theo creating a psychic bond, sinking claws into his neck. Theo can send this thoughts to Derek and can see what Derek sees. This week Theo's picked a skeezy ABS. Derek fights instruction at first but is helpless when he's told how good he is. Derek reluctantly hands over his clothes and kneels in the dark booth but smiles shyly when he's rewarded with a 'good boy'.

**Notes for the Chapter:**

> Praise Kink, Glory Hole, Telepathic Bonds, Anonymous Sex, Mind Control, Slut Derek, Exhibitionism, Sex Tape, Public Sex
> 
> This is NOT noncon. Derek agrees to the bond and for his memory of the event to be erased. He even records a message. Can potentially be considered dubcon as with his memory erased he doesn't know that.

When Theo's claws sank into Derek's neck, second thoughts began to surface. Still, before they were fully formed, they were replaced with more potent ideas, happier images, more dominant concepts. Whatever Theo wanted, Derek now dared to see through with just a little mental nudge. He hated to disappoint. It wasn't long after that he received his first test.

The pack had been meeting for lunch and afterwards were spending the afternoon in Lydia's favourite coffee shop. Derek had some errands to run and would return later, most notably for Theo's devious mind were the items needed from the hardware store for the loft. There were two reasons for that. First: once he'd grown bored of the second reason the actual shopping list for fixing walls and the electrics would be replaced in Derek's mind with the burning need to purchase more suggestive items; chains, heavy-duty screw eyes, rope, carabiners, clamps, fishing weights. Second: the fact that two doors down from the hardware store was an adult book store. That presented the perfect opportunity to test his newfound control over his toy and how well the sensory feedback worked.

Theo had been quite clear when Derek had agreed to this that he would implant suggestions, cajole, and even force his will. While claws were hovering at the back of his neck, Derek said his piece to camera, just in case they needed to show it was a free choice. They sank in. Once the bond snapped into place, only an act of will from Derek of significant strength would be able to overpower the new little voice in his head. Not that he'd know that; Theo wiped the memory of the creation of the bond. Which is why, a slightly confused expression on his face, Derek kept on walking, past the entrance to the hardware store, to the unassuming storefront on the corner with blacked-out windows.

Despite having no idea what he was doing, a voice in the back of his head walked him through paying the entry fee and going into the rear. It was bizarre. These weren't his own thoughts, but there was a compulsion to follow them. They even began to excite him, knowing where he was and would they were expecting of him. The first attempt to fight back came when, in front of a sign ordering clothes on outside the booths, the voice said, _'strip now. Here.'_

Derek pushed back in his mind, refusing the instruction. It filled his mind again, louder this time, angrier. Even as Derek began to think about a more assertive refusal, his shirt was already pulled up and off, and he'd started undoing his pants. _'You're going to learn to follow my orders my dirty little slut, or you'll be punished. This is your only warning, I hope it's sufficiently humiliating.'_ Completely naked and rock hard Derek gathered up his discarded clothes from the filthy floor and began to walk back out to the front of the store. No matter what he tried, he couldn't stop his feet from moving.

The clerk wasn't really paying attention until Derek coughed lightly. Looking up the man sighed, 'for fucks sake. Can none of you perverts read? Clothes on...'

'Outside the booths,' Derek finished, bored. Gesturing to himself, he asked, 'you really think this is going to harm business?'

The guy cocked an eyebrow. 'You always this up yourself?'

Whatever was holding Derek's mind hostage seemed to release slightly, as if seeing what he would do. It was somewhat terrifying as he realised a need to see this through. 'I'd prefer something else up myself. Lots of things actually.' Derek licked his lips and leant over the counter. 'Maybe you'd like to try it first?'

'Err...' began the slightly baffled reply before the clerk caught himself. Looking around the room, he smirked. 'Actually, it looks like you're going to be popular and I like it messy. How about I go last?' With that, Derek's clothes were taken from his and hidden under the counter.

A quick turn of his head confirmed it. At least a dozen men were staring at him hungrily, and soon he'd have them all. 'Deal.'

_'Good boy!'_ The voice in his head sounded saccharine and teasing, but Derek preened at the praise.

'Use booth four,' the clerk said. 'There's a hole for each end in from three and five.'

'You heard him, boys!' Derek shouted over his shoulder to the rest of the men, making his way back towards the booths. 'Head's in three and tails in five, pick a hole and fill me up!'

_'Oh, you're a very good boy. I can't wait to see how much cum you take you perfect dirty slut!'_ Derek's cock started to drip. Whatever it took to please his new conscience was worth it for the warm tingling feeling that came with the encouraging praise. Even the mocking was enjoyable.

The booth was dark when Derek entered it, the only light coming from the dimly lit corridor and through the two hip height holes connecting to the adjoining booths. Without bothering to close the door or put any money in the meter, he knelt on the sticky floor in the gloom and waited. _'Such a desperate slut. Not even bothered to turn the light on. You're supposed to put money in the machine you know, renting the booth. And leaving the door open so everyone can see you. Perfect!'_

Booth five had the first customer, a long thin cut cock. It was on the 'tails' side, but as it was dry, Derek thought a bit of spit was in order and quickly took it into his mouth. While he got accustomed to swallowing around a cock lodged in his throat, his fingers pulled back his own foreskin. They gathered up the slimy liquid that had been pooling inside as his cock leaked and reached back to rub the precum into his hole. To his surprise, he found himself already slicked. Then the memory returned. For no good reason, and yet without realising anything was off, he'd fingered himself open after his shower and had made sure to use plenty of Crisco. _'Because you're a slut, Derek. You were preparing yourself for this.'_

It was true. Before the next man even had the chance to stick himself through the hole, Derek had heard the 'heads' booth fill and pulled his mouth off the cock he'd been sucking. Spinning and holding it in one hand, he guided it to his hole and slowly sank back until his ass came up against the cold of the wall. Leaning over and using his arms to brace against the other side, his mouth pressed to the opposite hole, and a shorter, fatter cock slid into his mouth. It didn't matter what it looked like, or who it belonged to. All that mattered was that cum filled him, and its owner left satisfied. That his owner was satisfied. _'That's it pup. Learning your place, keeping me happy.'_

Derek began to rock back and forth, making sure to slap into the wall as the man breeding his ass thrust forward. The feeling of being filled nine inches deep, even if it wasn't that thick, had him moaning and slobbering around the piece stretching out his mouth. Seconds later Derek was choking as cum shot out of the stubby dick to hit the back of his mouth. _'That's a good slut. Swallow his load.'_ Derek gulped down the salty treat, and the cock withdrew. Seconds later another took its place, somewhere in between the two, longer than the first he'd sucked, thicker than the one in his...cunt? _'Oh, that's a good little fuck toy. You know exactly what your hole is don't you, think it again.'_ Muscles contracting around the man behind tipped him over the edge, for the first time in his life, Derek's cunt was filled with hot cum. _'Good boy.'_

Over and over mouth and ass were filled, load after the load was spilt into him. Derek couldn't be sure, but part of him thought if he had been human, this would have damaged him. All that shot through him were pleasurable sensations, each salty treat that emptied down his throat made him moan and whimper for more. It should humiliate him or feel degrading, but it didn't matter that he'd been bred by anyone who'd stick there dick in him, it all fed the voice that called him, _'good boy.'_

When no one else replaced the last to that pulled out, it made him whimper, not sure what to do. _'Remember you made a deal for this, Derek. Good boys follow through.'_ As cum dripped from his hole and his legs shook from exertion, he made his way down the corridor back to the front room of the shop. The same clerk was behind the counter, smirking at him. There was a 'phone set up on a tripod. As Derek walked up a sheet of paper and a pen was pushed towards him.

'There's a camera in booth four. Sign that, and bend over the end of the counter.'

_'I think you should do it,'_ the voice in his head whispered. _'But find out where he's going to post it. As much fun as it is, knowing your slutty escapades are going to be online for the world to see, it'll be so much better reading all the comments. Maybe someone you know will see it.'_

Derek braced himself over the counter, chest pressed against the cold glass top, peering down at plugs, cock rings, and vials of head cleaner. Without thinking he signed. 'Whatever you do with the footage, I want to see it.'

The clerk nodded and made his way behind Derek. Nothing was said, no warning was given. A huge cock, bigger than any he'd taken all night began to press inside, making his lips burn with the stretch. It seemed slow, despite the difficulty, at least until it had bottomed out. Then, there was no mercy. Pounded hard, the cock drove in and out, making Derek whimper in delicious agony. No matter how hard it went, he couldn't close his eyes, too busy staring into the 'phone's camera lens, biting his lip and hoping he looked like a desperate whore. When, finally, the thrusts turned erratic, and the clerk let out a loud roar as he shot, Derek smiled. This is what I'm made for; _'this is what you're made for.'_ Both thoughts ran through his head together.

A glass plug was pushed inside him. 'On the house.'

In a daze, Derek wandered through the hardware store picking things up, not really sure why unable to reconcile them with the work that the loft desperately needed. The checkout girl gave him odd looks as she rang up his purchases. It was more expensive than expected. More odd looks came when he re-joined the group in the coffee shop. Stiles asked him something about building a sex dungeon. Derek said, 'yes.' Everyone laughed, except Theo. He was just smiling smugly and watching Derek.

_'My good, filthy little pup.'_

Oh.


	31. Day 30 - Sex Toys | Deep Throating | Stuck In Wall

**Summary for the Chapter:**

> Monster of the Week in a sex shop. MoW goes through a wall into the next shop. Ethan jumps through and kills it, Derek dives after him but get his fat ass stuck on the girders. Ethan thinks it's funny until Derek goes from embarrassed to shocked. Jackson starts playing with Derek, demonstrating all the toys. Ethan's a bit unsure until Derek starts to whine.

**Notes for the Chapter:**

> Sex Toys, Deep Throating, Stuck In Wall, Fucking, Situational Humiliation
> 
> Warning dubcon - Jackson assumes consent, it is given

'Remind me why the fuck we're doing this again?' Jackson complained. Again.

'Because leaving a rabid Skeksis running around town is bad for the relaxed family-friendly nightlife?' Ethan's response was more than a little sarcastic. Part of the reason they worked was his ability to stoically weather Jacks' bitching.

'Yeah, no. Why are we here? And what, actually, the fuck are we chasing?' Finger quotes were used to emphasise the 'we' and Ethan could see Derek's eye start to twitch.

'Because Scott's off looking for another Omega with Chris and the rabble of misfit toys. Stiles is in Manchester with Lydia, and incidentally, they haven't been able to identify it, so we have no idea. And Jordan is on shift dealing with actual human problems,' Derek ground out. 'Also, no one invited you.'

'You turned up at our door begging for help,' Jackson countered. Sometimes Ethan was sure he did it just to be contrary and provoke a reaction. Ethan was going to do the right thing; let this play out and see if he could salvage some entertainment for the evening.

'No,' said Derek, emphatic. 'I politely requested Ethan's assistance. He agreed. I distinctly recall saying "for fuck's sake" when you insisted you were going to tag along. Also, I own your door.'

'So now we're roaming around the counties largest sex shop?'

'Maybe you can find something that Ethan will find more interesting than a monster hunt,' Derek said smugly.

'Fuck you, Hale. Fuck you.'

Ethan chuckled and then decided that the glare from Jackson wasn't worth it. 'So, in the interests of prolonging this entertaining sideshow and only picking a side out of my sex life's sense of self-preservation...Jackson, have you not seen what's in the grey bags Derek's been hiding in his room every evening when he comes home?'

'I had to buy them!' Derek protested, a flush rising on his face. 'Christie said I was starting to creep her out and if I didn't buy anything I'd have to leave.'

At Ethan's snickering, Jackson asked, confused but intrigued, 'buy what? And who's Christie?'

'Derek's been coming here every day for two weeks, that'd daily, trying to track this monster down.'

'Wait…you mean Derek got yelled at by a shop assistant for being a creeper, and his solution was to buy a sex toy every day? He's even on a first-name basis? That's fucking hilarious!' The braying laughter from Jackson let then know just how amusing he found it.

At Derek's thoroughly embarrassed expression, Ethan felt a tad regretful. It was just an unfortunately specific shop that had needed casing. It wasn't like Derek was buying stuff to use himself… 'Oh!' Derek winced at the exclamation, a small whine squeezing from his throat. 'Oh, Derek, it's normal. Jackson would have laughed at you even if it was a sporting goods shop. It's not like he's that big an asshole on purpose anymore.'

'Hey!' The retort was more confused than indignant, but at least it stopped the braying.

'I was annoyed when she confronted me, just picked something random of a shelf. She asked me if I was stalking her.'

'Why?' Jackson asked, more curious now.

'I'd been in three days in a row and when she told me to buy something or leave I picked up a Rabbit and said no when she asked me if I was getting it for my girlfriend. I needed to keep coming back, so I told her I didn't know what I was doing, what I was looking for, and that it had been a while. She picked out a silicone dildo and some lube and told me that if I came back the next day I either had to want something specific or I had to tell her what it felt like so she could find me something else. I needed to come back to try and identify or locate the creature. But, I didn't think I could fake a description and after two hours online looking at toys…it just seemed easier to try it.' Derek looked thoroughly miserable.

Jackson, on the other hand, looked thoughtful, and to Ethan's eye a little bit devious, but not cruelly so. Softly he said, 'and you came back. Because you liked it. You wanted more.' Derek looked like he was going to argue or tell Jackson to fuck of, but before he could, Ethan stepped in.

'Tell us what you told her. What did she pick out next?'

Derek was baffled into complying more than anything else. They both seemed genuinely curious, not like they were trying for ammunition to humiliate him later. 'I've never, you know...'

'Been with a guy?' Jackson asked.

'No, I've been with guys,' Derek replied matter of factly, not noticing the looks the other two shot each other. Nor did he see the conversation of raised eyebrows that was going on behind his back as they continued searching around the darkened store for any clue to the beast's location. 'They just always assume I'm a top. It becomes a self-fulfilling prophecy. I've never really had anything in there except my fingers sometimes.'

'So what was like,' Jackson said, a bit breathily and impatient.

'Weird,' Derek replied, unknowingly disappointing the couple. Before they could chime in through, he continued. 'No matter what I did, I couldn't get it to reliably hit against my prostate doing it myself, and I was getting frustrated. I like feeling full but needed more. I kind of liked it...the frustration kept me on edge without tipping over.'

'And you told her that? This Christine,' Ethan asked.

Butting in Jackson demanded, 'what was next? What did she suggest when you told her that?'

'I have no idea why I'm telling you any of this,' Derek grumbled. 'A prostate massager. She thought that if the dildo was getting me that close but not worked up, I should see if that pushed me over. She wanted to know if I could orgasm like that without touching my...you know. And either way, whether I preferred that or frustration.'

'And?'

'And I did. Orgasm. Three times. In a row. In less than half an hour.'

Ethan was becoming uncomfortable by this point. More due to tight jeans than anything else. 'So which did you prefer? That, or the frustration?'

Derek shrugged, and his blush returned. 'Both. After the third time, I switched to the dildo, for an hour. I was crying at that point. So I used the massager again and came a fourth time. It was still in when I woke up.'

'That was the fourth day, yeah?' Jackson queried. At the affirmative nod, it was easy enough to put two and two together. 'Oh my god! The next morning. You said you'd been overtraining.' Jackson actually seemed impressed.

'I don't get it,' Ethan said.

Grumbling, Derek explained, 'we went running, and I was a bit sore. Nice sore, but it was a bit uncomfortable.'

'Dude. You worked your ass over so hard your super-healing hadn't fixed it by the next morning.' For some reason that excited Jackson, more so when Derek started to look shifty.

Ethan picked up on it. 'Or...that doesn't really sound right does it. I wonder if someone slowed their healing on purpose just to feel the ache in their ass a bit longer.'

Derek blushed hotter, but this time seemed to realise they were doing it out of love rather than any intention to screw him over. 'I liked being rough. Keeping the toys in. Making the feeling last as long as I could,' he explained.

'Derek, I think you're a natural-born bottom,' Jackson proclaimed. 'What other toys did you get?'

Before Derek could reply, Ethan's hand shot up, stilling them instantly. They listened, straining their hearing. Slowly they looked up. The sound was almost imperceptible, a slight scratch of something moving in the ceiling, stalking. No further warning came before the monster burst through the tiles, taking a light fitting and part of the suspended ceiling structure with it. Derek was knocked over, and the gnarled vulture-like beast flattened Jackson before scrambling off through the store, Ethan in chase close behind it.

Derek was the first to give pursuit after a cursory check, and a returned nod, showed Jackson to only be winded and embarrassed. He caught the sight of the two taking the stairs back down to the first floor and ran to follow. Towards the back of the store, it seemed Ethan had the beast cornered, but it didn't slow and slammed into the wall. Instead of getting knocked senseless, it tumbled through the gap and Ethan, not slowing dived through after.

The second Derek's feet left the floor, he realised his mistake. A steel beam in between two concrete pillars began to slide down into the gap that he'd gauged just big enough to get through with maybe a jarred shoulder and some scratches. Knocking his broad frame against the pillars on his way through just sped the collapse of the beam, and whatever was above it. Luckily on the other side, the creature had quickly been dispatched by Ethan, and the nightlife of Beacon Hills was secure from supernatural threats for another week or two. Sometimes he really couldn't work out what possessed him to come back to this godforsaken town. Derek's hips were stuck fast, pinned down by rubble. His upper body rested on a counter on the newly opened side of the hole, and his ass hung in the sex shop. Thankfully his feet were touching the ground, so neither side was floating in the air.

'Oh this is just too perfect,' the muffled voice of Jackson sounded from behind.

'Get me the fuck out of here,' Derek tried to growl. It was mostly a meek whine. This was incredibly humiliating; there he was, thinking nothing would top the sexual escapades explanation portion of the evening. Whilst he could see the funny side he wasn't really feeling it at the moment. It regulated his temper somewhat though, as he only wanted to slightly rip Ethan's throat out when he started to chuckle.

'Stuck?'

'Fuck you.' Derek said with a snort of laughter seeping in. Then his face morphed into one of shock.

'Tell me no,' they heard from Jackson's side of the wall and Derek...Derek couldn't. Ethan looked confused until the moan ripped out of Derek and then it was his turn to be shocked, realising what Jackson must be doing. Ethan's phone beeped.

[From: Godzilla] His ass is unbelievable, swallowing up all these toys. Fucking his throat yet?

Derek was biting his lip, and his fingers were curled around the edge of the counter gripping so tightly they'd turned white. His eyes were closed, and every few gasps of air that were drawn in, his eyes rolled back behind his lids. Ethan really wanted to know what Jackson was fucking him with.

[From: Ethan] srsly jacks?hes wining .practically drooling

The urge to do as Jackson suggested was strong. It would be a lie if Ethan said he's never fantasised about getting to sample Derek. Really, who hadn't? But, he also knew that kind of objectification bothered the man, especially when it came from people he trusted, so it was always kept bottled up.

[From: Godzilla] Get your cock out and slide in. Bet he opens up at that end just as well.

Ethan wanted to, badly. His cock was straining against the fly of his too-tight jeans. But he couldn't really do it on the say-so of Jackson just because Derek hadn't said no to a question muffled through a wall. That thought threw some cold water over his desperation but barely dented his desire.

[From: Ethan] i duuno this is a bit much. r u sure es ok with thus

[From: Godzilla] Learn to type. Take your dick out, let him smell you and ask him if he wants it.

'Derek,' Ethan whispered, moving closer to the counter. Derek's head was at just the right height, chin just clearing the end of the countertop his chest was resting on. His eyes flew open to stare back at Ethan. 'Do you really want this?' Derek's gaze dropped to the bulge threatening to burst through denim and licked his lips while his nostrils flared. 'I need you to say it, Derek, I need to hear your heart when you say it.'

The answer was quiet, self-conscious, but sure. 'Please, I want it.'

No uptick in his heartbeat, and Ethan had shed his shirt and began fighting with the button of his pants. Once he had them open, he wasted no time pushing them down, just whipped out his cock and balls and left them within inches of Derek's waiting mouth.

Like Derek, Ethan, being a born werewolf, was uncut. His cock was long and thick and dripping with precum, the slit visible were the skin had pulled back slightly. Derek was sure that it would choke him if he tried to take it all, but when his nose filled with the scent of Ethan's strong musk, he didn't care. 'Fuck my mouth, Ethan, please,' he whimpered. 'Don't hold back.' Hands held the sides of Derek's head, and the exquisite taste burst over his tongue before the massive dick began to force its way slowly into his throat. It kept going until his nose rested in the nest of Ethan's pubes. With Jackson pressing some kind of vibrating toy against his prostate in some sort of sexual torture, Derek was in heaven.

[From: Godzilla] Eth?

[From: Ethan] oh fuk he's so hot and took me straight down to the base

'Let me know when you're ready to flood his mouth. I want to shove my cock in his hole while he's choking on your cum,' Jackson spoke out loud. Derek keened around Ethan at the suggestion and the vibrations running over his dick drew him up to the edge.

'I'm going to cum!' He yelled. A second later Derek roared around him, Jackson must have pressed inside. It was enough to tip Ethan over, and with one last deep thrust, he began to shoot deep in the contracting throat. Slowly he pulled back allowing Derek to recover from his choking and to taste the last few spurts that oozed out onto his tongue. Ethan let the suckling continue until it became too much for his sensitive cock and pulled out, tucking himself back away. Squatting down level with Derek's head, Ethan drew him into a long, slow kiss, sharing the taste of him. It wasn't long before whimpering signalled the jackhammering Jackson tended towards when he was close; then the sound of his roar through the wall.

'Want to get out of there now?' Ethan asked.

Derek still had a blissed-out look on his face. 'Fuck. Soon. Once Jackson's finished with his tongue in my ass.'

'Oh. Yeah, he can do that for hours. Wait 'till he uses his snake tongue.' Ethan was starting to chub up again, but they really needed to clear out of here soon.

For a minute Derek enjoyed the warm wet probing sensations then whined as the feeling changed, the stretch grew wider. 'He's pushing a plug inside me,' he gasped.

'Keeping his cum inside you so you're all sloppy when we get home and we both fill you up again. Would you like that, Derek? Do you love that plug keeping you stretched open?'

'Yes,' came the hissed reply. 'Please, Ethan. Love you two. Love toys too.'

'Don't even care you haven't cum do you? Hasn't even crossed your mind that we're just going to tuck your raging boner back in your jeans and leave you wanting.'

A high pitched whine spilt out. 'Please.'

'Fuck, Derek, you'll have to introduce us to this Christie. Toys are more fun when you share them with your friends, and we'd love to teach you what we know.'

'But the monster's dead. We don't need to come back.' Derek seemed confused and upset by the realisation.

Ethan planted a peck on now pouting lips and spoke in reassurance. 'You will, though.'

'Yes.' It was emphatic and sure. Derek would keep coming back here until he'd run out of thing to try.

'We love you too, Derek, you know that right?'

'I know. Ethan?'

'Hmm?'

'Get me the fuck out of this wall. And if Jackson has taken pictures, I will kill him.'


	32. Day 31 - Free Day | Autofellatio | Bukkake

**Summary for the Chapter:**

> It's the free day and final chapter, and...
> 
> As I didn't get a better offer...
> 
> Welcome to the Derek Hale Naked Yoga School: Flexing For Auto-Fellatio 101  
> Beginners Welcome!  
> Extra Credit Available (just ask Teach' >;[ )
> 
> Caught sucking himself while listening to music too loud (hence the catching), Derek ends up roped into teaching yoga to horny college kids who are oversexed and won't leave him alone.

**Notes for the Chapter:**

> Free Day, Autofellatio, Bukkake, Voyeurism, Exhibitionism, Group Sex, All on One, Bottom Derek, Size Queen, Self Sucking, Slut Derek
> 
> Lydia likes to watch but doesn't take part. Everything is consensual.

> **Welcome to the Derek Hale Naked Yoga School: Flexing For Auto-Fellatio 101**
> 
> **Beginners Welcome!**
> 
> **Extra Credit Available (just ask Teach' >;[ )**

Derek's eye twitched reading the notice pinned to the sliding door of the loft. Crudely drawn in crayon, it mocked him. Stiles must have been the one to make it. No one else would dare, at least not without forgoing making it look like it came from a five-year-old. On the way up the stairs, the heartbeats were clearly audible; rapid from fear or excitement he wasn't sure. All Derek knew was that he really didn't want to be doing this, even though he would anyway. With a sigh, the sign was ripped down, and the door slid open to reveal his students: Lots of students.

* * *

In a testament to his own lectures in being aware of your surroundings being sound advice, he now regretting wearing earphones during 'Derek's special alone time'. The main benefit of being Derek during his 'special alone time' was the ability, sat down, or on his back, to contort himself into the relatively comfortable position of deep-throating himself. It wasn't even that he was that large, just incredibly flexible. It was ten per cent genetic slash werewolfism and ninety per cent extensive yoga regime. The main drawback of being Derek during his 'special alone time' was the ability to attract people who were allergic to the concept of personal space with an inability to call in advance. Unless it suited them, of course.

All else being equal, he still wasn't sure if Death Cab for Cutie was appropriate listening material for pleasuring oneself. It was suggested by his 'phone, and he remembered liking it. Unfortunately, it was good at blocking out the world around him. At least to the point that he wasn't aware a slack-jawed Stiles was stood six feet away from him watching as he swallowed around himself and began to rub his fingers over his hole. If he hadn't have pulled back to adjust slightly, his balls hanging over his nose likely would have continued to block off the distinctive new scent that had entered the room. It was the first time Derek had ever choked on himself. Embarrassingly, he also couldn't stop himself from cumming as their eyes met. Carefully hidden but a mile wide the exhibitionist streak just couldn't let that one pass without more humiliation than the situation initially warranted.

What followed appeared to be an intervention. Derek assumed, initially, to get him laid, so he didn't need to keep doing that to himself. It actually turned out to be a pressure group demanding the technique be taught. That had been Stiles, Scott, Liam, Theo, and Isaac who'd returned with Chris the last time he'd been back to France. Putting up a token protest, he had little reason to say no. They were trying to convince him using all the same arguments he'd made in the past for physical conditioning. They even managed it without bringing up the fact that they really wanted to get their own dicks in their horny mouths.

* * *

So now Derek found himself sliding open the loft door to be faced with the original five conspirators and their five new recruits. The two extra couples, Jackson and Ethan, and Mason and Corey, at least made some kind of sense. But, Lydia? Derek suspected this group had more to do with Stiles' ability to keep his mouth shut and less to do with active recruitment of participants.

'You do know what they're all here for, right?' He asked her and received a contemptuous stare in return.

'Of course,' Lydia replied, primly.

Derek really didn't care. 'So are you joining in or...?'

'Hmph,' was the indignant reply. 'I'm here to observe. The kinesiology interests me. Also, I don't really have the equipment, do I?'

'Depends how flexible you are,' he said, matter-of-factly. The slightest flush rose on Lydia's cheeks made him smirk. 'And I don't really care. I'm not shy.'

'Perhaps we could discuss private lessons. To determine feasibility.'

Derek shrugged. 'Okay.' The boys were all looking back and forth throughout the exchange. Most not really following what was being implied. At least until it clicked with Stiles.

'Wait. Are you? If you're watching this can we watch...'

'No!' The emphatic refusal came from Lydia and Derek at the same time.

'That is so unfair,' mumbled Stiles.

'Do you lot want me to teach you to suck your own dicks or not?' That was a sentence Derek never thought he'd say. At the various nods and affirmatives, he added, 'then get you clothes off. And I don't care if Lydia stays.'

'Wait,' Scott meeped. 'I thought Stiles was joking! We're really doing this naked?' Apparently, that hadn't been obvious to everyone as evidenced by the contagious blush that was spreading around. Ironically it seemed that the new coupled additions and Isaac from the original group were the only ones who didn't seem phased.

'How the hell else are we supposed to get out dicks in our mouths?' Isaac asked baffled.

Mason chimed in next, with Corey nodding along beside him. 'Yeah, when Stiles and Scott told us Derek was going to teach us "naked yoga for self-sucking" we kind of figured it would be, you know, naked.'

Jackson was already stripped down to his boxers and rolling his eyes hard; it would give mere mortals brain damage. 'The moron twins strike again. I expect it from Scott, but Stiles? Jesus!' Ethan wasn't far behind in disrobing.

Derek just sighed in put-out resignation. 'Strip, or, unless your name is Lydia, leave. I hope you thought the yoga part of naked yoga meant yoga, because I've only got one mat and I'm telling you now, concrete is not your friend.' He began to shed his own clothes, stripping off his shirt as he made his way to the bed area. When he returned with his mat from where it was stored underneath, everyone had stripped down with varying levels of reluctance and rolled out their mats.

'Fuck my life,' Derek thought. Then, out loud, he said, 'okay, the rules. No jokes, no comments. You need to be comfortable to do this, and at the moment most of you aren't. If you can't relax for this, you won't get very far. If you want to make fun of each other's dicks or who has hair where or cracks about skipping leg day, do it somewhere else. Do it here, and you're out. Understood?'

They all mumbled various affirmatives, but all of them, surprisingly, especially Jackson, seemed to take the rule and the threat seriously.

'Second: what we're doing is about you and your body and your pleasure, but it's also inherently sexual. It will help if we pair off which for the couples shouldn't be a problem, but for the rest, it will involve at minimum intimate touching. Anyone not comfortable with that?'

There were some shifting eyes and sly glances. It was Stiles that eventually piped up. 'Look I'm not averse to...' He wiggled his fingers. 'Touching anyone in this room as long as it's nice and consenty, except for Scott.'

'Hey,' came the indignant and hurt interjection.

'Because the interrupter is like my brother and it will feel really, really weird.'

'Oh. Yeah, gross.'

'Thanks, Scott. So I have two questions. Who wants me and who gets Derek? There are five of us. Unless the couples are mixing it up. But then there's still nine which is also an odd number unless somebody pairs with the teacher.'

'Stiles.' Derek growled. 'I really hope you're a natural at this.'

'Really? Thanks! Why, though?'

'Because your mouth will be full and you won't be able to talk,' Lydia muttered.

Stiles looked like he was preparing a reply, luckily Theo turned to Isaac and Liam. 'I'll take Stiles. Liam with Scott. Isaac, Derek? Or shall we rock, paper, scissors?' Liam nodded and moved next to Scott while Theo took his place next to Stiles.

Derek raised his eyebrow at Isaac. 'You sure...'

'It's fine, Derek. Really.' Isaac smiled, and his heartbeat was steady. At Derek's nod, he moved as well.

'Okay. We're going to go through some basic asanas, stretching out, getting comfortable with being naked. I'll be looking for relaxation and natural ability. We'll move on to some more focused positions to stretch out the lower back and hips. And if anyone's close, we can try getting them over the line and coming up with specific focussed stretches for the individual. Otherwise, we'll just keep working on stretching, and I'll give you some asanas to practice. We can meet as often as you want, but even for the wolves, it's going to take weeks or maybe months. Some of you might never be able to do it.'

'And if none of them even get close today?' Lydia asked, seemingly genuinely curious.

Derek shrugged. 'Then I'll give you a demonstration. You've probably all seen it in internet porn. I know Stiles has seen it in real life because after twenty-two years on this earth he still doesn't know how to call ahead or wait to be invited in when he actually bothers to knock.'

'In my defence, this is the result,' Stiles motioned around the room with swinging arms, one of which came perilously close to whacking Theo in the balls.

'That way,' Derek continued as though he hadn't been interrupted. 'You'll be able to see that it is possible and that if you put in the work, you can actually achieve it. Everyone ready?'

At nine answering nods, he began with deep breathing in Tadasana, then down to Virasana and further breathing and relaxation. Given that they next pushed into the downward-facing dog, in their current state of dress, this was where Derek had been expecting the maturity level to suddenly plummet. To his pleasant surprise, everyone stayed quiet and just pushed down into the stretch. The assholes on display and dangling genitalia didn't really seem to faze anyone.

Having them walk their legs in then rise into Surya Namaskar and tree pose, one leg then the other, brought about the first erections. The twitching of supernaturally powerful noses picking up on the growing arousal in the room created a kind of feedback loop. Derek stood before them left foot against his right knee, cock jutting out six inches from its hairy thatch, but everyone's eyes were off to his left. Curious, he turned his head slightly to see what was fascinating them and swallowed audibly. Isaac stood serenely in the same pose, firmly planted without swaying in the slightest. A knowing yet somehow not smug smirk lit up his lips. Sticking out from a patch of blonde curls, pale like the rest of him, his hardness stood straight out, as long again as Derek's own. Still, no one said anything, though Jackson and Theo both couldn't help licking their lips.

It continued for some time, moving from one stretch to the next. Making sure everyone was at least able to perform the basic version of each form before moving onto the next was usually straight forward. For some reason it was a pleasant experience, despite it being hands down the weirdest bonding experience Derek had ever partaken in. Where possible his preference was to get lost in the movements and let them flow until the sense of peace and relaxation radiated throughout his entire body. But this time he was conscious of the rest of the group possibly having other plans and the humans, in particular, hitting up against a wall of sudden exhaustion. By this point, everyone was remarkably sweaty. It was a smell Derek enjoyed, and his cock twitched.

'Time?' he mouthed silently to Lydia, who seemed to be watching him knowingly. Despite not having any particular attraction to her the undeniably voyeuristic nature of her clothed presence and his own exhibitionist streak flared, and he twitched again. Leaking this time onto the foam mat. She smirked and held up her 'phone for him to see the time, unrepentant in the face of his raised eyebrow. They'd been going nearly two hours. For today at least, it was time to move onto the finisher.

Moving into Halasana, Derek took a swipe at his own head to scoop out the build-up of precum under his foreskin. Ostensibly it was to stop it dripping onto his face, but it tasted magnificent as usual. After a few seconds, he realised he could no longer hear breathing and unfolded to see ten pairs of wide eyes glued to his body. Maybe it should have bothered him, but he was nothing if not comfortable in his own skin even if his mind still proved troublesome. The spell broke, and they all began to attempt the position. This would separate the natural talent from the possible and the probably not.

Isaac had no trouble getting the first two inches into his mouth, but that was down to his size, not his flexibility. Derek's hand pressing on his lower back eased in another inch, but there was too much strain on the neck and not enough bend in the backbone. Derek showed him some spine openers to work on and surveyed the rest of the room.

Jackson, Theo, and Corey were the only three who's dicks were shorter than Derek's own. Jackson it seemed was a natural and despite slightly less than six inches of cock was less than an inch from his lips and within reach of his tongue. Derek would have a private chat with Ethan about how to help Jackson get further. A hole on display like that and so close, a warm wet tongue could do wonders. Corey was quite flexible but had a shorter back than Jackson and lacked the length at his groin. At about four inches it seemed he was the smallest of the bunch, and also the point of rule one. Derek could take his dick being called tiny by the right partner any day of the week, but he didn't want anyone else feeling shitty about theirs. With practice, Corey would get in at least far enough to nurse his head.

The straightness in Theo's back made Derek wince. All through the session, he'd seemed to struggle more with flexibility than anyone else had. It was a toss-up whether he would ever make it and it would require consistent work. All of the rest? They were in various stages of getting there to almost got it. Scott and Stiles were both the closest contenders to Isaacs gargantuan length but needed to work on stretching out some. Even for human Stiles, the two of them would probably be there in less than a month. Liam and Ethan were perhaps the average for the group in terms of length and would both be sucking their own dicks soon enough.

Despite Isaacs...impressive showing, it was Mason that turned out to be the star of the show. His knees were touching the mat on either side of his head, and his back was bowed in the same way Derek's did. Seemed they had a supernatural self-sucker among them with the length to make it look good, and it turned out to be one of the humans. Mason's hands were gripping his ass hard, pulling down on his hips as his head and neck rose up on each downstroke. Each thrust was forcing at least four inches inside and on every dozen or so bobs it went deep enough that it gagged him slightly. The show was beginning to attract a crowd until all ten were watching. It turned out Derek wasn't the only exhibitionist present. When Mason's eyes opened to see ten pairs of staring back and eight hard cocks pointing his way, he came. The first few shots were a surprise which made him choke slightly. Still, he allowed his hips to rise, pulling back slightly and finishing on his tongue before slowly letting himself uncurl. Breathing heavily, he swallowed. 'Thanks, I'm glad I came.'

The group burst out laughing making Mason blush at the double entendre. 'You did good,' Derek said with a smile. 'But I'm pretty sure all of you can manage it, some of you just need more work than others.'

'Like me,' Theo said, slightly put out and rubbing his back, but grinning none the less.

'So,' Lydia said, startling everyone. 'Has Mason ruined it for everyone by being especially proficient, or do we still get a demonstration from the master?'

'It's Lydia's fault for qualifying "if none of them even get close today",' Jackson griped. Looking so incredibly put out, Derek couldn't help a wide grin at his expense and the urge to indulge them.

'Fine, but no cameras. I trust Lydia not to be so stupid, but with the rest of you, it's anyone's guess. What do you want me to do?'

Most of them seemed confused, as though it was apparent. 'Do what you like to do,' Theo said.

'Yeah,' Ethan murmured his voice gravelly. 'Pretend we're not here. Just do what you'd do to make yourself feel good.'

'I feel like this is moving beyond a practical demonstration into sexual voyeurism, but I've already seen it once, and I really would like to see it again. And if you aren't going to film it, then live action it is.' Stiles was unrepentant even as some gazes appeared to be questioning his sanity.

Derek just shrugged. 'Like I said, I'm not shy, and this is inherently sexual. Just because you can get your dick in your mouth doesn't mean it's the end of it. Besides, Stiles is right, it is voyeuristic, and I like being watched or...' Derek cut off.

'Or?' Isaac asked softly.

'Or...audience participation is welcomed but not mandatory.' Derek said with a shudder.

'What does that mean?' Liam asked, curious.

Lydia was looking between Isaac and Derek, who were staring at each other. 'May I suggest, so no lines are crossed that cannot be uncrossed that it means bukkake for all but Isaac.' They kept staring at each other until they nodded.

'I've changed my mind.' Derek said to disappointed groans, but he ignored them. 'Lydia, your 'phone has a better camera. Anyone who's going to join in has a problem with that?'

All their heads shook, and Derek sank to his mat. Slowly he lifted his leg to point his toes straight up then said, 'Isaac, nightstand, top drawer.' His legs tipped back, lifting his hips and slowly, he began to curl his back as they came closer to his face. About halfway down, Derek started to spread his knees outwards, and they hit the ground with the tip of his throbbing cock touching his chin. Squeezing his muscles caused it to bob into position for him to catch it on his tongue. Arms hooked over the backs of his thighs and hands pressing into his lower back, he slowly fed his dick into his mouth. Tasting his precome once again made him moan, and the sucking started in earnest, digging the salty nectar from under his foreskin and flooding his mouth with saliva in response.

A tap to his thigh forced him to open his eyes, and a pot of creamy lubricant floated in mid-air. He took it, careful not to unfold at the release of his arms and slicked up the fingers of both hands. Slowly and carefully, they began to probe his hole as they also pulled him further down. At the same time, his neck started to lift, bobbing along his length. After a dozen stokes like this, his nose buried in his pubes and all of him was inside. When the head pushed into his throat, only his experience prevented him from gagging and choking on his juices.

Fingers poked and prodded at his hole, slowly working on stretching himself wide. Derek slipped the first two fingers of his right hand in with barely any resistance and pressed the tips into his prostate. As it forced more liquid to spurt from his slit, he moaned around his cock and began to massage the sensitive spot. Without waiting, the same fingers, from the other hand, worked to push in alongside spreading himself open. If he understood the shared looks with Isaac and the implication behind Lydia's words, he'd need to open himself up.

'Open your eyes, Derek,' Lydia's voice broke through his reverie as he stretched and sucked. His eyes opened. All of them, to a man, stood around him, jerking themselves frantically as they watched. Stood over his ass and looking down into his eyes was Isaac, calmly and slowly stroking his foot long monster. Thinking about it splitting him open had Derek moaning around himself once more. The were vibrations making his hole twitch, particularly when Corey and his cute little dick were the first to tip over the edge. It became clear they weren't planning to target his face.

Stepping up close and aiming at Derek's hole, Corey shot of spurt after spurt of a surprisingly large load crying out as he shook with it. Each splatter slicked up Derek's fingers, and the slide into his hole became easier. So easy in fact that when Isaac kneeled and slipped two long fingers deep inside taking the total to six, Derek barely felt the stretch. Scott and Theo were next to shoot, and at least one of them was a heavy cummer. Isaac had to work to scoop the mess up and push it inside Derek's now gaping hole. When no one else seemed ready to blow, Isaac then took the opportunity to taste.

Precome was flooding Derek's throat as his first-made beta's tongue licked around his straining muscle and dipped inside. Isaac had knocked Derek's own fingers out by now, replacing them with more of his own. Only his thumbs were outside rubbing drops of saliva and semen into the skin as he pulled the hole wide open. When Jackson signalled his need to blow, Isaac pulled back at kept the target open. Ethan followed quickly after, then together Stiles and Liam.

Now it was Isaac's turn. He stood, looking down at Derek, staring into his eyes as his mouth and throat worked around the length of his own cock. Isaac began to squat until his cock head pressed into the slicked and messy hole and started to push in. It was a long slow fall, and at halfway, Derek's eyes slipped closed against his will. Isaac kept on coming. The angle felt odd, it made it easier for the huge cock to make its way in but also seemed like it was going to meet his own coming out of his throat. Isaac had to bend over for the last few inches, placing his hands on the backs of Derek's calves and pushing his legs further down. That and the weight of Isaac against his hips sent Derek's cock impossibly farther down his throat, as deep as he's ever taken it.

It wasn't going to last long from the stimulation from the autofellatio, stroking, and the fact that this was Derek Hale, but Isaac began to pump his hips. Using his bent legs for leverage, it made it possible to pull out around eight inches and be able to power back in. From the constant droning Derek was making, vibrating around his own cock and clenching feebly around Isaac it seemed the pile driving in plough pose was a hit. Derek went first, shooting straight down his throat and some combination of the spluttering and the spasming ring around the base of his cock had Isaac following a few strokes later. After a moment to get back his breath, he pulled himself up and out, not wanting Derek to start choking. He needn't have worried.

Rising up to his knees, Derek quickly took the messy and barely shrinking cock deep into his throat. Cleaning off the taste of his own ass and the soup of cum that had slicked its way and stuck to the flesh as it was churned up made him crazed. After minutes of this, he let it drop from his mouth, as soon as Isaac's breathy moans turned to whimpers. He collapsed back down onto his back, worn out, and cum dripping from his hole.

'Derek,' Jackson said, sounding impressed. 'You're a bona fide slut aren't you.'

'Mmm,' he agreed, momentarily rendered insensible. Then, because he couldn't pass up the opportunity. 'Takes one to know one.'

'Hey, Derek?' Stiles asked, uncharacteristically unsure of himself.

'Stiles?' Derek asked, tired.

'Could you teach me yoga? You know, actual normal clothed yoga, with the calmness and the breathing? I...I felt calm. Didn't feel the need to speak, was able to focus. On my breathing and your instructions, I mean. Not giving myself head.'

'Sure. Anyone else too, if they want. It'll help with this, but it's not the main reason I do it. I get stuck in my head too. I just don't vomit a stream of consciousness over everyone else.'

'Har har. Thanks, though.' At Derek's nod in reply, Stiles' focus shifted. 'Weren't you going to invite Danny?' he asked, curious.

'I did,' Jackson grouched.

Ethan huffed out a laugh. 'Apparently, he doesn't need lessons. Jacks' is a bit put out that Danny didn't share this knowledge earlier.'

'Huh,' Stiles mused. 'I wonder if I'm attractive to gay guys yet.'

'Yes,' came the put upon chorus from at least five of the attending. Except for Ethan, they were all bi or pan, but they supposed it didn't hurt to boost his ego if they could actually claim attraction to males. Even Derek threw his voice into the mix.

It has been an eventful evening for sure.

* * *

A knock sounded at the door. Derek sighed, having only gotten out of the bath a short while ago. At least this time he hadn't started and they'd bothered to respect his privacy. Answering the door in nothing but his poorly fastened fluffy dressing gown brought him face to face with Chris Argent. He was rubbing the back of his neck sheepishly, and a blushing Jordan Parrish was beside him, standing in Derek's doorway.

'So,' Chris began. 'Derek. We were wondering?'

'Wondering what.' This was not what he had expected of the evening.

'Wondering whether there's an upper age limit? Or if you're doing evening classes?' Chris asked smirking.

Derek bit his lip. 'I think I can manage that. Maybe a more hands-on approach.'

'Oh we're counting on it,' Chris said, a hand pushing Derek back into the loft as Parrish slid shut and bolted the door behind them.

**Notes for the Chapter:**

> If you have read any of this, thank you and I hope you enjoyed it.  
> If you have made it through all 31 chapters extra thank you's!  
> If you left kudos super thank you's and...  
> If you took the time to comment I really appreciate it. I write because I like to but it's nice to know others enjoy what I've written.
> 
> Next year I'll start this earlier. Might actually finish before November!

**Author's Note:**

> Kudos and comments are appreciated but don't feel obligated! :)
> 
> I'm also on twitter @bgiific


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